1-Chloro-3-phenylpropan-2-one → 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-phenyl-2-propanon-1-yl)oxybenzamide

HRID 620269Notes

Reaction equation

HRID 620269 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.Cl[CH2:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>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:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 2363491-Chloro-3-phenylpropan-2-oneHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 141168964-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-phenyl-2-propanon-1-yl)oxybenzamideYield 40.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the tetrabutylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (3.45 g, 6.5 mmoles) and 1-chloro-3-phenyl-2-propanone (1.1 g, 6.5 mmoles) in acetonitrile was stirred for 18 hours at 20°. After removal of the acetonitrile at reduced pressure, the residue was treated with water and extracted with methylene chloride. The residue, after concentration of the extracts, was chromatographed on alumina (grade III) using ethyl acetate from elution. Combination of the appropriate fractions gave 1.1 g of product which was recrystallized from ethyl acetate to give the title compound, mp. 138°-139°.

Workup

  1. customAfter removal of the acetonitrile at reduced pressure
  2. additionthe residue was treated with water
  3. extractionextracted with methylene chloride
  4. customThe residue, after concentration of the extracts, was chromatographed on alumina (grade III)
  5. washfrom elution

Sources & evidence

ORD record
ord-096fc38335f94d96a4a887d93103b67b
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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