1,1'-Thiocarbonyldiimidazole → 1-(4-Isothiocyanatophenyl)-4-(1-isobutyl)piperazine

HRID 2213899Notes

Reaction equation

HRID 2213899 reaction equation
[CH2:1]([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)[CH:2]([CH3:4])[CH3:3].[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]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)=[C:18]=[S:19]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 219589424-(4-Isobutylpiperazin-1-yl)aniline

Product 1

HCID 98786871-(4-Isothiocyanatophenyl)-4-(1-isobutyl)piperazineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 4-[4-(isobutyl)-1-piperazinyl]benzenamine (7.8 g, 33.4 mmol) (from Step B above) in N,N-dimethylformamide (75 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (5.97 g, 33.5 mmol) (Aldrich) in N,N-dimethylformamide (25 mL). After the addition was complete, the mixture was stirred at −15° C. for 20 min, the cooling bath was removed and the solution was stirred for 1 h. Ice-water (700 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-(1-isobutyl)piperazine (8 g, 87%)

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 h
  4. additionIce-water (700 ml) was added
  5. stirringthe mixture was stirred for 30 min
  6. filtrationThe solid was filtered off
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-81eafddff9ec478893a9a794345eb42f
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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