1-Isocyanato-4-methoxybenzene → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]-propyl}-3-(4-methoxyphenyl)urea hydrochloride

HRID 543172Notes

Reaction equation

HRID 543172 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.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=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:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)=[O:29])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 13606667HCID 13606667, compound

Product 1

HCID 136066841-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]-propyl}-3-(4-methoxyphenyl)urea hydrochlorideYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 3 was followed, using 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (5.09 g; 19 mmole), methylene chloride (50 ml) and 4-methoxyphenyl isocyanate (2.83 g; 19 mmole). Recrystallization from methanol/methylene chloride provided the title compound (3.57 g; 45% yield) as orange-white crystals, m.p. 237°-238° C.

Workup

  1. customRecrystallization from methanol/methylene chloride

Sources & evidence

ORD record
ord-9a72fc3f4ed6425b9a83eec8cf992cdf
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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