4-Chlorophenyl Isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-chlorophenyl)urea hydrochloride

HRID 1380183Notes

Reaction equation

HRID 1380183 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>C(Cl)Cl>[ClH:18].[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:27]([NH:26][C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=3)=[O:28])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 136066801-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-chlorophenyl)urea hydrochlorideYield 48.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 3 was followed, using 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (2.67 g; 10 mmole), methylene chloride (50 ml) and 4-chlorophenyl isocyanate (1.54 g; 10 mmole). Recrystallization from methanol provided the title compound (1.1 g; 25% yield) as colorless crystals, m.p. 241° C.

Workup

  1. customRecrystallization from methanol

Sources & evidence

ORD record
ord-70c095fb218541028b89adcc5823fe8c
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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