| Identification | More | [Name]
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide | [CAS]
364-62-5 | [Synonyms]
2-Methoxy-5-Chloroprocainamide
4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxy-benzamid
4-amino-5-chloro-n-(2-(diethylamino)ethyl)-n-anisamid
4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamid
4-Amino-5-Cholo-N-[(2-diethylamino)ethyl]-2-methyloxy-benzamide
5-Chloro-2-methoxyprocainamide
Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-
DEL
DEL 1267
del1267
Metaclopramide
Metaclopromide
Methochlopramide
Methoclopramide
Metochlopramide
Metoclol
Metoclopranide
Metocobil
Metramid
Moriperan | [EINECS(EC#)]
206-662-9 | [Molecular Formula]
C14H22ClN3O2 | [MDL Number]
MFCD00211338 | [Molecular Weight]
299.796 | [MOL File]
364-62-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white, fine powder. | [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 | [InChI]
InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19) | [InChIKey]
TTWJBBZEZQICBI-UHFFFAOYSA-N | [SMILES]
C(NCCN(CC)CC)(=O)C1=CC(Cl)=C(N)C=C1OC | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white, fine powder. | [Originator]
Primperan,Delagrange,France,1964 | [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. |
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