4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE)
Moclobemide
CAS: 71320-77-9
Molecular Formula: C13H17ClN2O2
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Names and Identifiers
| Name | Moclobemide |
| Synonyms | MODOBEMDE moclbemide Moclobemide p-Chlor-N-(2-morpholinoethyl)benzamid 4-Chloro-(2-(4-morpholinyl)ethyl)benzamide 4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide Benzamide, 4-Chloro-N-(2-(4-morpholinyl)ethyl)- benzamide, 4-chloro-N-[2-(4-morpholinyl)ethyl]- 4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide, Aurorix, Moclamine Ro-11-1163, Aurorix, Manerix, Moclamine, p-Chloro-N-(2-morpholinoethyl)benzamide |
| CAS | 71320-77-9 |
| EINECS | 629-727-7 |
| InChI | InChI=1/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17) |
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Physico-chemical Properties
| Molecular Formula | C13H17ClN2O2 |
| Molar Mass | 268.74 |
| Density | 1.206±0.06 g/cm3(Predicted) |
| Melting Point | 137°C |
| Boling Point | 447.7±40.0 °C(Predicted) |
| Flash Point | 224.6°C |
| Solubility | DMSO: >20mg/mL |
| Vapor Presure | 3.29E-08mmHg at 25°C |
| Appearance | solid |
| Color | white |
| Merck | 14,6226 |
| pKa | 14.26±0.46(Predicted) |
| Storage Condition | room temp |
| Refractive Index | 1.55 |
| MDL | MFCD00865388 |
| Physical and Chemical Properties | Crystallization from isopropanol, melting point 137 °c. Acute toxicity LD50 rats (mg/kg):707 oral. Moclobemide Hydrochloride: C13H17C1N2O2? HCl. Crystallization from isopropanol, melting point 208 °c. |
| Use | Used as an antidepressant |
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R26/27/28 - Very toxic by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S22 - Do not breathe dust. |
| UN IDs | 3249 |
| WGK Germany | 2 |
| RTECS | CV2462000 |
| HS Code | 29349990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in rats (mg/kg): 707 orally (Burkard, Wyss) |
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Standard
Authoritative Data Verified Data
This product is 4-chloro-n-[2-(4-morpholinylethyl)] benzamide. Calculated as dried product, the content of C13H17C1N202 shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline or crystalline powder; Odorless.
- This product is soluble in methanol, ethanol or chloroform, dissolved in acrylic rain, slightly soluble in water, soluble in glacial acetic acid.
melting point
The melting point of this product (General rule 0612 first method) is 136~140°C. Absorption coefficient take this product, precision weighing, plus 0.lmol/ L hydrochloric acid solution is dissolved and quantitatively diluted to prepare a solution containing about lOug per lml, and the absorbance is measured at the wavelength of 240nm by ultraviolet-visible spectrophotometry (General rule 0401), the absorption coefficient is 557 to 591.
Last Update：2022-01-01 11:53:06
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.721 ml | 18.605 ml | 37.211 ml |
| 5 mM | 0.744 ml | 3.721 ml | 7.442 ml |
| 10 mM | 0.372 ml | 1.861 ml | 3.721 ml |
| 5 mM | 0.074 ml | 0.372 ml | 0.744 ml |
Last Update：2024-01-02 23:10:35
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Differential diagnosis
Authoritative Data Verified Data
- take about 10mg of this product, add 5ml of dilute hydrochloric acid and 20ml of water to dissolve, and take 5ml of bismuth potassium iodide solution 2 drops to generate orange-red precipitate.
- the solution under the term of absorption coefficient has the maximum absorption at the wavelength of 240nm as determined by ultraviolet-visible spectrophotometry (General rule 0401), there is minimal absorption at a wavelength of 214nm.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 740).
Last Update：2022-01-01 11:53:07
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Exam
Authoritative Data Verified Data
alkalinity
take l.Og of this product, add 10ml of water, silence for 10 minutes, filter, take the filtrate to measure according to law (General rule 0631),pH value should be 7.3~8.5.
chloride
take 0.60g of this product, add 50ml of water, shake for 5 minutes, filter, take 25ml of filtrate, check according to law (General rule 0801), and compare with the control solution made of 6.0ml of standard gasification sodium solution, no more concentrated (0.020%).
sulfate
take 2.0g of this product, add 50ml of water, ultrasound for 5 minutes, filter, take 25ml of filtrate, check according to law (General rule 0802), compare with the control solution made of ML of standard potassium sulfate solution, no more concentrated (0.030%).
Related substances
take this product, add the mobile phase to dissolve and make a solution containing 1.5mg per lml, as a test solution; Take the appropriate amount of precision, A solution containing 15mg per 1 ml was prepared by dilution with the mobile phase as a control solution. According to the high performance liquid chromatography method (General 0512) test, using cyanosilane bonded silica gel as filler; 0.14% triethylamine solution [phosphoric acid solution (1-2) the pH was adjusted to 6.0]-methanol (65:35) as the mobile phase; The detection wavelength was 235mn. The number of theoretical plates shall not be less than 2000 calculated as per moclobemide peak. 20 u1 of control solution and 20 u1 of test solution were respectively injected into human liquid chromatograph, and the chromatogram was recorded to 2.5 times of the retention time of principal component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (0.5%) the area of the main peak of the control solution, and the sum of the areas of each impurity peak shall not be greater than the area of the main peak of the control solution (1.0%).
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
arsenic salt
take this product l.Og, add lg of calcium hydroxide, mix, add a small amount of water, mix evenly, dry, burn with small fire to charring, burn at 500~600°C to completely Ash, cool, add hydrochloric acid 5ml and water 23ml to dissolve, check according to law (General Principles 0822 The first law), should comply with the provisions (0.0002%).
Last Update：2022-01-01 11:53:07
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Content determination
Authoritative Data Verified Data
take this product about 0.2g, precision weighing, add glacial acetic acid dissolved in 20ml, add crystal violet indicator solution 1 drop, with perchloric acid titration solution (0.1 mol/L) titration to a blue color of the solution, and the results of the titration were corrected by a blank test. Per 1 ml perchloric acid titrant (0.1 mol/L) corresponds to 26.87mg of C13H17C1N202.
Last Update：2022-01-01 11:53:08
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Category
Authoritative Data Verified Data
antidepressants.
Last Update：2022-01-01 11:53:08
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:53:09
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Moclobemide tablets
Authoritative Data Verified Data
This product contains moclobemide (C13H17C1N202) should be 93.0% ~ 107.0% of the label amount.
trait
This product is white or white-like tablets or film-coated tablets, film-coated tablets after removal of white or white.
identification
- take an appropriate amount of fine powder of this product (about 50mg of moclobemide), put it in a 25ml measuring flask, add an appropriate amount of ethanol, and shake to dissolve moclobemide, dilute to the scale with ethanol, shake, filter, take the continued filtrate as the test solution; Take another moclobemide reference, add ethanol to make a solution containing 2mg per 1 ml, as a control solution. According to the thin layer chromatography (General 0502) test, absorb the above two solutions of 15 u1, respectively, on the same silica gel GF 254 thin layer plate, with ethyl acetate-ethanol-concentrated ammonia solution (8:2:1) for the development of the solvent, expand, dry, set the UV lamp (254nm) to view, the position and color of the main spot of the test solution should be consistent with the main spot of the reference solution.
- take the solution under the content determination item, according to UV-visible spectrophotometry (General 0401), there is a maximum absorption at the wavelength of 240nm, there is minimal absorption at a wavelength of 214nm.
examination
- dissolution of this product, according to the dissolution and release determination method (General 0931 first method), with 0.lmol/ L hydrochloric acid solution 900ml as the dissolution medium, the rotation speed is 100 revolutions per minute, according to the operation, after 30 minutes, take the appropriate amount of solution, filtration, precision take the appropriate amount of filtrate, with 0. The 1 mol/ L hydrochloric acid solution is made into a solution containing about 10ug of moclobemide per 1 ml, and the dissolution amount of each tablet is calculated according to the method under the content determination item. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product (film-coated tablets to remove coating), precise weighing, fine grinding, precise weighing appropriate amount (about equivalent to 20mg of moclobemide), and put it in a 100ml measuring flask, add 0.1 mol/L hydrochloric acid solution appropriate amount, shake to dissolve the benemide and dilute to the scale, shake, filter, take the continuous filtrate 5ml, put it in a 100ml measuring flask, use 0. Dilute the lmol/L hydrochloric acid solution to the scale, shake well, and measure the absorbance at the wavelength of 240mn by UV-Vis spectrophotometry (General rule 0401), precision weighing, add 0. lmol/L hydrochloric acid solution was dissolved and diluted quantitatively to prepare a solution containing about 10ug per lml, which was determined by the same method. It is obtained by calculation.
category
Same as moclobemide.
specification
(l)75mg (2)0.lg (3)0.15g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:53:09
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Moclobemide capsules
Authoritative Data Verified Data
This product contains moclobemide (C13H17C1N202) should be 93.0% ~ 107.0% of the label amount.
trait
The content of this product is white or white powder.
identification
- take an appropriate amount of the contents of this product (about 50mg of moclobemide), put it in a 25ml measuring flask, add an appropriate amount of ethanol, and shake to dissolve moclobemide, dilute to the scale with ethanol, shake, filter, take the continued filtrate as the test solution; Take another moclobemide reference, add ethanol to make a solution containing 2mg per 1 ml, as a control solution. According to the thin layer chromatography (General 0502) test, absorb 15ul of each of the above two solutions, respectively point on the same silica gel GF 254 thin layer plate, with ethyl acetate-ethanol-concentrated ammonia solution (8:2:1) for the development of the solvent, expand, dry, set the UV lamp (254nm) to view, the position and color of the main spot of the test solution should be consistent with the main spot of the reference solution.
- take the solution under the content determination item, according to UV-visible spectrophotometry (General 0401), there is a maximum absorption at the wavelength of 240mn, there is minimal absorption at a wavelength of 214nm.
examination
- dissolution of this product, according to the dissolution and release determination method (General 0931 second method), with 0.900ml of lmol/ L hydrochloric acid solution is the dissolution medium, and the rotation speed is 50 revolutions per minute. The operation is carried out according to law. After 30 minutes, the appropriate amount of the solution is taken, filtered, and the appropriate amount of the filtrate is taken, A solution containing about 10ug of moclobemide per 1 ml made of 0.1mol/ L hydrochloric acid solution was measured according to the method under the content measurement item, and the dissolution amount of each particle was calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
take the contents under the difference of loading amount, mix evenly, weigh an appropriate amount (about 20mg equivalent to moclobemide) accurately, put it in a 100ml measuring flask, add 0.1 mol/ L hydrochloric acid solution appropriate amount, shake to dissolve the benemide and dilute to the scale, shake, filter, take the continuous filtrate 5ml, put it in a 100ml measuring flask, use 0. Dilute lmo1/ L hydrochloric acid solution to the scale, shake well, measure absorbance at the wavelength of 240nm by UV-Vis spectrophotometry (General rule 0401), precision weighing, add 0.lmol/ L hydrochloric acid solution was dissolved and diluted quantitatively to prepare a solution containing about 10ug per lml, which was determined by the same method. It is obtained by calculation.
category
Same as moclobemide.
specification
O.lg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:53:10
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE) - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Overview | a novel monoamine oxidase inhibitor moclobemide is a reversible selective oxidase inhibitor. It has no early monoamine oxidase inhibitors (MAOI) such as isopropyl hydrazine, phenethyl hydrazine and other side effects such as "cheese" reaction, high blood pressure risk phase and serious liver damage, the antidepressant is characterized by selective inhibition of monoamine oxidase type A, while increasing the levels of norepinephrine, dopamine and serotonin in the brain, resulting in an antidepressant effect. |
| effect | and can improve sleep quality, no effect on vigilance or short or long memory, and can reduce the impact on the recognition function. In anti-depression, anti-hypoxia and other aspects of curative effect is remarkable, especially suitable for with heart, kidney disease in elderly patients with depression. Its curative effect is exact, the clinical safety is good, the effect spectrum is wide, is superior to the other antidepressants in clinical application. |
| preparation | (1) synthesis of bromoethylamine hydrobromide at -5 ℃-0 ℃, 40% hydrobromic acid was added to the raw material ethanolamine, m hydrobromic acid: m ethanolamine = 5: 1, and the temperature of the system was controlled to not exceed 0 °c. After the addition was completed, the reaction was continued to stir for 0.5h. After completion of the reaction and distillation under reduced pressure, white needle-like crystals were obtained, and the melting point of the product was 70-71 °c. The same amount of 40% hydrobromic acid as above is added dropwise to the reaction system. After the addition is completed, 100-150ml of The Solvent xylene is added, and the mixture is heated and refluxed for 20-24H at 120-128 ℃, and the solvent is distilled under reduced pressure, the product was poured hot and washed twice with cyclohexanone to obtain a white crystalline product, 2-bromoethylamine hydrobromide, with a melting point of 168-170 °c. (2) synthesis of 4-chloro-n-(2-bromoethyl) benzamide 2-bromoethylamine hydrobromide was added with 5 times (m: v) amount of water, Stir to dissolve. An equimolar amount of P-chlorobenzoyl chloride and 10% NaOH solution with 2-bromoethylamine hydrobromide was added dropwise at -5 °c. After completion of the dropwise addition, the reaction was stirred at low temperature for 1H. Filtration with water gave 4-chloro-n-(2-bromoethyl) benzamide as a white solid. (3) synthesis of moclobemide 4-chloro-(2-bromoethyl) benzamide to add 7 times the molar amount of morpholine, stirring reflux, temperature 123-125 ℃, after 10-12H reaction, cool down, add water and 5%NaOH solution to adjust the pH value to 11, filter and wash with water, recrystallize petroleum ether twice to obtain white solid moclobemide with melting point of 137.5~138.5 ℃, the content was 99.60%. |
| antidepressants | Moclobemide, English name is moclobamide, chemical name is p-chlorobenzamide, it is A reversible inhibitor of selective monoamine oxidase-A developed by Roche in 1990. Mainly used for unipolar and bipolar endogenous depression, deep or chronic non-endogenous depression. It has no early monoamine oxidase inhibitors (MAOI) such as isopropyl hydrazine, phenethyl hydrazine, such as the use of "cheese" reaction, hypertension risk phase and serious liver damage and other side effects, the antidepressant is characterized by selective inhibition of monoamine oxidase type A, and can improve sleep quality, and has no effect on vigilance or short and long memory, and can reduce the impact on the recognition function. In anti-depression, anti-hypoxia and other aspects of curative effect is remarkable, especially suitable for with heart, kidney disease in elderly patients with depression. Its curative effect is exact, the clinical safety is good, the effect spectrum is wide, is superior to the other antidepressants in clinical application. The product is now available in more than 50 countries. |
| pharmacological action | This product is monoamine oxidase inhibitor (MAOI), by reversibly inhibiting type a monoamine oxidase (MAO-A), the levels of norepinephrine (NA), dopamine (DA) and 5-hydroxytryptamine (5-HT) in the brain are increased, resulting in an antidepressant effect. Compared with irreversible MAO I, it has the characteristics of fast inhibition of enzyme and fast recovery of MAO activity after drug withdrawal. |
| Use | is indicated for the long-term treatment of endogenous depression, mild chronic depression, psychogenic or reactive depression. The selective reversible inhibitor of monoamine oxidase A has less side effects and is well tolerated, and can be used by both the old and the young. For a new generation of antidepressants, but also for the treatment of children with attention deficit hyperactivity disorder. used as antidepressant |
| pharmacokinetics | absorption was rapid and complete after oral administration, F = 80%,Tmax = 0.3~2 h, t1/2 is 1~3 h, PPB is 50%. Widely distributed. Almost all from the liver metabolism, metabolism by the liver after rapid excretion by the urine. Only a small part of the original form of excretion from the kidney. Because of its rapid metabolism, it is often necessary to adjust the dose at the beginning of treatment. |
| synthetic route | 1. Preparation of N-(2-hydroxyethyl) P-chlorobenzamide (2): to the three-necked flask, P-chlorobenzoic acid methanol and concentrated sulfuric acid were sequentially added, and the mixture was refluxed for 4H. The methanol was distilled off under reduced pressure, ice water was added, stirred, filtered, and washed with cold water to obtain a white solid. It was added to the reaction flask, ethanolamine and appropriate ammonium chloride were added, refluxed for 3H, cooled, poured into ice water, filtered, and washed with 5% sodium hydroxide and anhydrous ethanol to obtain white crystal 2. 2. Preparation of N-(2-chloroethyl) P-chlorobenzamide (3): add 2 and dichloromethane successively to the three-necked flask, slowly add thionyl chloride Dropwise, after dropping, the solution was reacted at 40-50 °c for 1H. After completion of the reaction, the residue was slowly added with ice water, stirred and filtered. The filter cake was washed with water until neutral, dried and recrystallized with toluene, white-like crystals 3 were obtained. 3. Preparation of moclobemide (1): 3, morpholine, anhydrous sodium carbonate and toluene were added sequentially to a three neck flask. Heated and stirred at reflux for 5H, cooled, filtered, the filter cake was washed with water until neutral, then recrystallized from 50% isopropanol aqueous solution, filtered and dried to give white crystals 1. Figure 1 is the synthesis of moclobemide |
| dosage | This product is an oral medication, oral: 300mg/d, can be increased or decreased to 150 ~ 600mg/d according to the disease. The elderly, renal function decline can not adjust the dose; Severe liver dysfunction, the dose can be reduced to 1/2~1/3. |
| adverse reactions | 1. Mild Nausea, dry mouth, Head Pain, dizziness, sweating, palpitation, Sleep Initiation and Maintenance Disorders, postural hypotension, etc. 2. Rare adverse reactions with allergic rash. 3. Occasional disturbance of consciousness, elevated blood pressure and liver function damage. 4. High dose may induce epilepsy. |
| note | 1. Severe hepatic and renal insufficiency should be used with caution. 2. This product is prohibited from being used simultaneously with other antidepressant drugs to avoid the danger of causing high serotonin syndrome. 3. The use of central analgesics (pethidine, codeine, dextromethorphan), ephedrine, pseudoephedrine or phenylpropanolamine in patients with prohibited this product. 4. If the patient has a tendency to turn to manic episode, the drug should be discontinued immediately. 5. It is not suitable to drive vehicles, operate machinery or work at height during medication. 6. Regular examination of blood and heart, liver and kidney function should be performed during medication. By other antidepressants to use this product, it is recommended to stop 2 weeks after the start of use of this product; Fluoxetine should be discontinued 5 weeks before starting to use this product. 8. Use with caution in pregnant women. Lactating women should stop breastfeeding when using this product. Use in elderly patients to reduce dosage as appropriate. |
| drug interaction | 1. Combination with cimetidine can delay the metabolism of this product. 2. The combination with cyproheptadine can prolong and strengthen the anticholinergic effect. Combined with carbamazepine, can cause acute hypertension, high fever, seizures. 4. Combined with droperidol, can increase cardiac toxicity. Combined with adrenergic beta 2 receptor agonist, can cause palpitations, agitation or hypomania. 6. With Anti diabetic drugs, due to the stimulation of insulin secretion, may cause severe hypoglycemia and other reactions. (2016-04-26) |
| overdose | 1. Performance: After Overdose, after about 12 hours of incubation period, the central nervous system excited state, performance agitation, sweating, tachycardia, muscle rigidity, hyperreflexia, delirium and high blood pressure and fever. Body temperature up to 40 ℃, diastolic blood pressure more than Head Pain mmHg(16kPa), there may be severe Vomit,, optic nerve head edema and epileptic seizures and other signs of hypertensive encephalopathy. A small number of patients with hypotension, respiratory depression and bleeding tendency. 2. Treatment: The following measures should be taken in a timely manner: ① timely gastric lavage, remove gastric poison; ② infusion and osmotic diuretic forced diuresis, urine acidification (can enter a large amount of vitamin C) is conducive to accelerate the excretion of drugs; ③Symptomatic treatment and supportive therapy were given according to the patient's condition. |
| production method | Method 1: bromoethylamine hydrobromide is dissolved in water and benzene, 5% sodium hydroxide is added dropwise, the aqueous layer was separated, pyridine was added, and p-chlorobenzoyl chloride was added dropwise at 25 °c. After refluxing and cooling, Suction filtration, washing, drying, recrystallization with benzene, amide product, yield 91.8%. The amide was stirred with morpholine and ethyl acetate, water was added and the pH was adjusted to 1-2 with hydrochloric acid. The ester layer was separated, extracted twice with ethyl acetate, and the aqueous layer was neutralized with 10% sodium hydroxide to pH 8-9. The solid was collected by filtration and recrystallized from isopropanol to obtain moclobemide of white needle-like crystals with a yield of 80.2% and a melting point of 136-137 °c. The total yield was 73.6%. The following operation may also be performed. The bromoethylamine hydrobromide was dissolved in water and p-chlorobenzoyl chloride and sodium hydroxide solution were added dropwise at 0-5 °c with vigorous stirring. The reaction continued, The amide product was obtained in 98.7% Yield. The amide and morpholine are stirred and refluxed to obtain moclobemide. The crude product is recrystallized from isopropanol with a yield of 75.3% and a melting point of 136~137 °c. The total yield was 74.3%. Method 2: Acrylamide is dissolved in water, and the addition reaction with morpholine is carried out at low temperature. The resulting morpholino propionamide solution was directly added into alkaline solution of sodium hypochlorite without treatment for Hofmann degradation. After post-treatment, morpholinoethylamine was obtained with yield of 42.3% and boiling point of 99~100 ℃/3.2kPa, nd201.4739. P-chlorobenzoic acid and ethyl chloroformate react in acetone solution in the presence of triethylamine to form ethyl p-chlorobenzoyl formate, which has a strong reactivity, reaction with the morpholinoethylamine obtained above gave moclobemide in 58.9% yield with a melting point of 136-137 °c. Although the reaction steps are longer, the raw materials used are simple. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-06-12 11:16:21
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View History
4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE)
5-三丁基锡-3,4-乙烯基二氧噻吩
FMOC-D-天冬氨酸-5-叔丁酯
5-甲酰基-2-噻吩羧酸
8-二羟基喹啉-2-甲酸
7-溴-5-甲基苯并[B]呋喃
3-羟基-N-(2-甲氧基苯基)-2-萘甲酰胺
NSC 95114-3C
四氯化钯二铵
生物素酰氨基己酰-6-氨基己酸N-羟基琥珀酰亚胺酯
5-三丁基锡-3,4-乙烯基二氧噻吩
FMOC-D-天冬氨酸-5-叔丁酯
5-甲酰基-2-噻吩羧酸
8-二羟基喹啉-2-甲酸
7-溴-5-甲基苯并[B]呋喃
3-羟基-N-(2-甲氧基苯基)-2-萘甲酰胺
NSC 95114-3C
四氯化钯二铵
生物素酰氨基己酰-6-氨基己酸N-羟基琥珀酰亚胺酯