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Metoclopramide → 4-[2-(4-chlorphenoxy)isobutyroylamino]-5-chloro-2-methoxy-N-[2-(diethylamino)-ethyl]benzamide

HRID 614807
Notes
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Reaction equation

HRID 614807 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([Cl:20])[C:14]([NH2:19])=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])[CH2:4][CH3:5].C(N(CC)CC)C.[Cl:28][C:29]1[CH:41]=[CH:40][C:32]([O:33][C:34]([CH3:39])([CH3:38])[C:35](Cl)=[O:36])=[CH:31][CH:30]=1.[OH-].[Na+]>O.C(Cl)(Cl)Cl>[Cl:28][C:29]1[CH:41]=[CH:40][C:32]([O:33][C:34]([CH3:38])([CH3:39])[C:35]([NH:19][C:14]2[C:13]([Cl:20])=[CH:12][C:11]([C:9]([NH:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:10])=[C:16]([O:17][CH3:18])[CH:15]=2)=[O:36])=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4168MetoclopramideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chloride

Product 1

HCID 131406634-[2-(4-chlorphenoxy)isobutyroylamino]-5-chloro-2-methoxy-N-[2-(diethylamino)-ethyl]benzamideYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6212ChloroformSolvent

Procedure

Metoclopramide (59.8 g.; 0.2 mole) and triethylamine (30.0 g; 0.3 mole) are dissolved in 400 ml. of chloroform. To this mixture there is added dropwise 2-(4-chlorphenoxy)-2-methylpropionic acid chloride (72.0 g.; 0.3 mole). The mixture is heated under reflux for two hours and is subsequently mixed with 100 ml. of 20% caustic soda solution and with water. After evaporation, the distillation residue is recrystallized from methanol whereby 73.2 g. (73.7% of theory) of 4-[2-(4-chlorphenoxy)isobutyroylamino]-5-chloro-2-methoxy-N-[2-(diethylamino)-ethyl]benzamide having a melting point of 120°-121° C. is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for two hours
  3. additionis subsequently mixed with 100 ml
  4. customAfter evaporation
  5. customthe distillation residue is recrystallized from methanol whereby 73.2 g

Sources & evidence

ORD record
ord-13329d2adcd34b1faab2c6dff917845c
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04146637

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes