Butyl isocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-n-butylurea dihydrochloride hemihydrate

HRID 1380176Notes

Reaction equation

HRID 1380176 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.[CH2:19]([N:23]=[C:24]=[O:25])[CH2:20][CH2:21][CH3:22]>C(Cl)Cl>[OH2:25].[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:24]([NH:23][CH2:19][CH2:20][CH2:21][CH3:22])=[O:25])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1.[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:24]([NH:23][CH2:19][CH2:20][CH2:21][CH3:22])=[O:25])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1.[ClH:18].[ClH:18]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 1317145951-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-n-butylurea dihydrochloride hemihydrateYield 213.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-aminopropyl)-4-(4-chlorobenzyl)piperazine (2.67 g; 10 mmole) in methylene chloride (50 ml) was refluxed for two hours with n-butyl isocyanate (1.09 g; 11 mmole). The reaction mixture was concentrated in vacuo, and the residue was treated with ethereal hydrogen chloride. Recrystallization of the precipitate from methylene chloride/methanol provided with title compound as colorless crystals (3.2 g; 71% yield), m.p. 222°-223° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with ethereal hydrogen chloride
  3. customRecrystallization of the precipitate from methylene chloride/methanol

Sources & evidence

ORD record
ord-b976ba6b379749e594794e7b30df558d
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

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