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

HRID 27718

Reaction equation

HRID 27718 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-adab6185963e48b29418236becec0751
Source dataset
uspto-grants-1980_09
Patent number
US04223034

Linked notes

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