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| | 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Basic information | | Uses |
| Product Name: | 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide | | Synonyms: | 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-n-anisamid;Methoxychloroprocainamide;Methoxychlorprocainamide;4-Amino-5-chloro-N-(2-diethylamino) ethyl-o-anisamide;Benzamide, 4-amino-5-chloro-N-2-(diethylamino)ethyl-2-methoxy-;Metoclopramide (base and/or unspecified salts);4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide;Metoclopramide | | CAS: | 364-62-5 | | MF: | C14H22ClN3O2 | | MW: | 299.8 | | EINECS: | 206-662-9 | | Product Categories: | PRANDIN;API;364-62-5 | | Mol File: | 364-62-5.mol |  |
| | 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Chemical Properties |
| Melting point | 146-148°C | | Boiling point | 418.7±45.0 °C(Predicted) | | density | 1.2432 (rough estimate) | | refractive index | 1.5200 (estimate) | | storage temp. | 2-8°C | | solubility | Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride | | form | neat | | pka | pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate) | | color | White to Off-White | | BRN | 1884366 | | CAS DataBase Reference | 364-62-5(CAS DataBase Reference) | | NIST Chemistry Reference | Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5) |
| | 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Usage And Synthesis |
| Uses | Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis. | | Chemical Properties | White or almost white, fine powder. | | Originator | Primperan,Delagrange,France,1964 | | Uses | Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis. | | Uses | antidiabetic | | Definition | ChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine. | | Manufacturing Process | The N-(diethylaminoethyl)-2-methoxy-4-aminobenzamide used as the starting
material may be prepared from o-toluidine. The o-toluidine is initially nitrated
with nitric acid to produce 4-nitro-o-toluidine. The 4-nitro-o-toluidine is then
converted to 2-hydroxy-4-nitrotoluene by heating with nitrous acid. By
reacting the resulting 2-hydroxy-4-nitrotoluene with dimethyl sulfate, 2-
methoxy-4-nitrotoluene is formed. The 2-methoxy-4-nitrotoluene is oxidized
with potassium permanganate to produce 2-methoxy-4-nitrobenzoic acid. The
latter substituted benzoic acid is treated with thionyl chloride to form 2-
methoxy-4-nitrobenzoyl chloride. A methyl ethyl ketone solution of the 2-
methoxy-4-nitrobenzoyl chloride is added over a period of about 1? hours to
a methyl ethyl ketone solution containing an equal molecular quantity of N,Ndiethylethylene diamine while stirring and maintaining the temperature
between 0°C and 5°C. The N-(diethylaminoethyl)-2-methoxy-4-
nitrobenzamide hydrochloride formed precipitates. It is filtered, washed twice
with methyl ethyl ketone, dissolved in alcohol, and reduced catalytically in an
absolute isopropyl alcohol solution to form N-(diethylaminoethyl)-2-methoxy-
4-aminobenzamide. The base is obtained by precipitating with sodium
hydroxide.
80 g (0.3mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide are
dissolved in small portions in 150 cc of acetic acid. The mixture is cooled and
45 g (0.45 mol) of acetic anhydride are added, and the solution obtained is
heated for two hours on a water bath. After cooling, the solution is decanted
into a round-bottomed flask with a stirrer, a thermometer and a tube for
introducing the chlorine. It is stirred and the current of chlorine is passed
through, the temperature being maintained between 20°C and 25°C. The
stirring is continued for one hour after the completion of the absorption of the
chlorine.
The mixture obtained is poured into 2 liters of water and the base is
precipitated with 30% soda. The precipitated base is extracted with 400 cc of
methylene chloride. After evaporation of the solvent, the N-(2-
diethylaminoethyl)-2-methoxy-4-acetamino-5-chlorobenzamide formed
crystallizes. The melting point is 86°C to 87°C and the yield is 95%.
To obtain the corresponding amino derivative, 109 g of base are heated under
agitation in a round-bottomed flask with 300 cc of 35-36% concentrated
hydrochloric acid and 600 cc of water. It is heated on a water bath until
dissolution is complete, then maintained at boiling point for 90 minutes,
cooled, diluted with 1 liter of water, and neutralized with about 350 cc of 30%
soda. The N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide
formed crystallizes, is centrifuged and washed in water. Its melting point is
122°C and the yield is 74%.
To obtain the corresponding dihydrochloride, the base is dissolved in absolute
alcohol (3 volumes) and to that solution is added 5 N alcoholic hydrochloric
acid. The dihydrochloride precipitates, is centrifuged and washed with alcohol.
It is a solid white material, having a melting point of 134°C to 135°C. | | Brand name | Maxolon (King); Reglan (Baxter
Healthcare); Reglan (Robins); Reglan (Schwarz Pharma). | | Therapeutic Function | Antiemetic | | General Description | Metoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children. |
| | 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Preparation Products And Raw materials |
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