Cyclohexyl isothiocyanate → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-cyclohexylthiourea

HRID 1380192Notes

Reaction equation

HRID 1380192 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.[CH:19]1([N:25]=[C:26]=[S:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[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][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[S:27])[CH2:6][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 14289Cyclohexyl isothiocyanateHCID 13606667HCID 13606667, compound

Product 1

HCID 136067181-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-cyclohexylthioureaYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Aminopropyl)-4-(4-chlorobenzyl)piperazine (5.36 g; 20 mmole) was reacted with cyclohexyl isothiocyanate (2.82 g; 20 mmole) in methylene chloride (35 ml) for two hours in the manner described in Example 17. The crude product was isolated and chromatographed on silica gel in analogous manner. The product, on recrystallization from ethanol, yielded the title compound (2.98 g; 36% yield) as colorless crystals, m.p. 127°-128° C.

Workup

  1. customThe crude product was isolated
  2. customchromatographed on silica gel in analogous manner
  3. customThe product, on recrystallization from ethanol

Sources & evidence

ORD record
ord-39f7cc4c96474379a68843e84ad1d634
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Reaction notes

Loading…