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

HRID 543174

Reaction equation

HRID 543174 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-02d1ffcb85b04d64807f20945821b51c
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Linked notes

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