1-Bromo-2-butanone → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-butoxy)-benzamide

HRID 1382966Notes

Reaction equation

HRID 1382966 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][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([OH:19])[CH:3]=1.Br[CH2:21][C:22](=[O:25])[CH2:23][CH3:24]>C(#N)C>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:21][C:22](=[O:25])[CH2:23][CH3:24])[CH:3]=1

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 141168934-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-butoxy)-benzamideYield 87.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the tetrabutylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (5.3 g, 10 mmoles) in acetonitrile (100 ml) was treated with 1-bromo-2-butanone (1.5 g, 10 mmoles) and stirred at 20° for 2 hours. The residue after concentration was treated with water and extracted with ethyl acetate and methylene chloride-2-propanol (5:1). The insoluble solid material was collected and combined with the organic extracts. Concentration of this mixture gave sticky crystalline material which was recrystallized from acetonitrile-water (4:1) to give the title product (3.1 g, 86%), mp. 103.0°-104.5°.

Workup

  1. concentrationThe residue after concentration
  2. additionwas treated with water
  3. extractionextracted with ethyl acetate and methylene chloride-2-propanol (5:1)
  4. customThe insoluble solid material was collected
  5. customConcentration of this mixture gave sticky crystalline material which
  6. customwas recrystallized from acetonitrile-water (4:1)

Sources & evidence

ORD record
ord-18009cea371a47ebadf77f209afdad40
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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