Potassium Hydroxide → N-(4-amino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide

HRID 1065954

Reaction equation

HRID 1065954 reaction equation
C([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[O:14])=[C:7]([O:28][CH3:29])[CH:6]=1)(=O)C.[OH-].[K+]>C(O)C>[NH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([NH:12][C:13]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:19][CH2:20]2)=[O:14])=[C:7]([O:28][CH3:29])[CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20538750N-(4-acetylamino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide

Product 1

HCID 20538744N-(4-amino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-acetylamino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide (e9) (1.4 g) in ethanol (20 ml) was refluxed for 1 hour with an aqueous (4 ml) solution of potassium hydroxide (0.6 g). The solvent was removed by evaporation and the residue extracted with ethyl acetate. Chromatography of the solution (on alumina with 5% water, in chloroform) followed by evaporation of the solvent yielded N-(4-amino-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide (e10).

Workup

  1. customThe solvent was removed by evaporation
  2. extractionthe residue extracted with ethyl acetate
  3. customChromatography of the solution (on alumina with 5% water, in chloroform) followed by evaporation of the solvent

Sources & evidence

ORD record
ord-34fefb64a5a64ca0b11e5648cb66a681
Source dataset
uspto-grants-1982_05
Patent number
US04331816

Linked notes

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