Chloroform → Metoclopramide

HRID 1733656Notes

Reaction equation

HRID 1733656 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([Cl:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(Cl)(Cl)Cl.[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][CH2:22][NH2:23])[CH3:19]>C(N(CC)CC)C>[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][CH2:22][NH:23][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:13])[C:10]([NH2:12])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 60993N,N-DiethylethylenediamineHCID 816264-Amino-5-chloro-2-methoxybenzoic acid

Product 1

HCID 4168MetoclopramideYield 60.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Methoxy-4-amino-5-chlorobenzoic acid (1.0 g) and 1-methanesulfoyloxy-1,2,3-benzotriazole (1.07 g) are suspended into chloroform (15 ml) and therto is added dropwise triethylamine (0.7 ml) with stirring under ice-cooling to give a clear solution. To the solution is added 2-(diethylamino)ethylamine (0.6 g) at room temperature and the mixture is allowed to stand for 18 hours. The solvent is then distilled off and thereto are added water and 1 N aqueous sodium hydroxide. The resulting crystals are separated by filtration, washed with water and then dried to give N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide (0.9 g), melting point: 145°-146° C. The product is identified with an authentic sample by infrared spectrum.

Workup

  1. temperaturecooling
  2. customto give a clear solution
  3. distillationThe solvent is then distilled off
  4. additionare added water and 1 N aqueous sodium hydroxide
  5. customThe resulting crystals are separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-db250146f73f470c953ef796ed32a455
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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