1,1'-Thiocarbonyldiimidazole → 1-(4-Isothiocyanatophenyl)-4-(sec-butyl)piperazine

HRID 2213895

Reaction equation

[CH:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)([CH2:3][CH3:4])[CH3:2].[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19]>CN(C)C=O>[N:17]([C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)=[C:18]=[S:19]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 4-[4-(sec-butyl)-1-piperazinyl]benzenamine (3.5 g, 15 mmol) (from Step B above) in N,N-dimethylformamide (40 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (2.68 g, 15.03 mmol) (Aldrich) in N,N-dimethylformamide (15 mL). After the addition was complete, the mixture was stirred at −15° C. for 20 min, then the cooling bath was removed and the solution was stirred for 1 h. Ice-water (800 ml) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with water and dried under vacuum to give 1-(4-isothiocyanatophenyl)-4-(sec-butyl)piperazine (3.6 g, 87%) as a purple solid.

Workup

additionAfter the addition
customthe cooling bath was removed
stirringthe solution was stirred for 1 h
additionIce-water (800 ml) was added
stirringthe mixture was stirred for 30 min
filtrationThe solid was filtered off
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-81deeb727c064360a6651c9aad3644ff
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105670B2

Linked notes

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