Metoclopramide → HCID 13140663, compound

HRID 614807

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

Participants

7

Reactant 4

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

Product 1

HCID 13140663HCID 13140663, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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
Patent number
US04146637

Linked notes

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