Sodium Hydroxide → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carboxyphenyl)urea hydrochloride

HRID 1380187Notes

Reaction equation

HRID 1380187 reaction equation
Cl.[Cl:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)=[O:19])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=3)=[O:19])[CH2:12][CH2:13]2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 202057461-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-ethoxycarbonylphenyl)urea hydrochloride

Product 1

HCID 202057421-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carboxyphenyl)urea hydrochlorideYield 146.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}-3-(4-ethoxycarbonylphenyl)urea hydrochloride (2.59 g; 5.6 mmole) in methanol (75 ml) was refluxed for 8 hours with aqueous sodium hydroxide (1N; 10 ml). The reaction mixture was concentrated in vacuo, and the residue was dissolved in water. After filtration, the solution was acidified with hydrochloric acid, and the precipitated solid was collected and washed with methanol to provide the title compound (1.92 g; 80% yield) as colorless crystals, m.p. 244°-246° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. filtrationAfter filtration
  4. customthe precipitated solid was collected
  5. washwashed with methanol

Sources & evidence

ORD record
ord-a5de3f42a3e34ca3a8f71be3fa4256bc
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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