Metoclopramide → HCID 14372582, compound

HRID 1382959Notes

Reaction equation

HRID 1382959 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14]C)[CH2:12]C)=[O:7])=[C:4]([O:19]C)[CH:3]=1.NC1C(Cl)=CC(C(NCCN(C)C)=O)=C(OC)C=1>>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:14])[CH3:12])=[O:7])=[C:4]([OH:19])[CH:3]=1

Participants

3

Reactant 2

HCID 4168MetoclopramideHCID 103785104-amino-5-chloro-N-[2-(dimethylamino)ethyl]-2-methoxybenzamide

Product 1

HCID 14372582HCID 14372582, compoundYield 89%

Procedure

The general procedure of Preparation 1A was repeated except that the 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide utilized therein was replaced by 4-amino-5-chloro-N-[2-(dimethylamino)ethyl]-2-methoxybenzamide (prepared according to U.K. Patent Specification No. 1,793,771). The solvent (DMF) was removed in vacuo, and the residue treated with water and methylene chloride saturated with carbon dioxide, concentrated, and the crude product isolated in 89% yield by extraction with ethanol. A sample was chromatographed on a silica gel column using methylene chloride (97), methanol (3), ammonia (0.3) solvent system. The appropriate fractions were combined and concentrated in vacuo. The residue was crystallized from methanol to give the title compound as a colorless solid, mp. 163°-165°.

Workup

  1. customThe solvent (DMF) was removed in vacuo
  2. additionthe residue treated with water and methylene chloride saturated with carbon dioxide
  3. concentrationconcentrated
  4. customthe crude product isolated in 89% yield by extraction with ethanol
  5. customA sample was chromatographed on a silica gel column
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-7ffef2c22a544e19a2fe147a01dd083a
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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