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

HRID 543179Notes

Reaction equation

HRID 543179 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-ea29a4606c3e43b0866290a4b03ca12c
Source dataset
uspto-grants-1987_04
Patent number
US04661481

Reaction notes

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