4-Methylphenyl isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-methylphenyl)urea dihydrochloride monohydrate

HRID 543171Notes

Reaction equation

HRID 543171 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.[C:19]1([CH3:28])[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>C(Cl)Cl>[OH2:27].[ClH:18].[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:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([CH3:28])=[CH:20][CH:21]=3)=[O:27])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 202057491-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-methylphenyl)urea dihydrochloride monohydrateYield 49.4%

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-tolyl isocyanate (1.33 g; 10 mmole). Recrystallization from methanol/methylene chloride provided the title compound (0.81 g; 17% yield) as colorless crystals, m.p. 131°-132° C.

Workup

  1. customRecrystallization from methanol/methylene chloride

Sources & evidence

ORD record
ord-c834e57e44f84496b839b73ca21367f0
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

Loading…