1,1'-Thiocarbonyldiimidazole → 4-Cyclopentyl-1-(4-isothiocyanatophenyl)piperazine

HRID 2213897Notes

Reaction equation

HRID 2213897 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[S:20]>CN(C)C=O>[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[CH:14][C:15]([N:18]=[C:19]=[S:20])=[CH:16][CH:17]=3)[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 91615544-(4-Cyclopentylpiperazin-1-yl)aniline

Product 1

HCID 99657194-Cyclopentyl-1-(4-isothiocyanatophenyl)piperazineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 4-[4-(1-cyclopentyl)-1-piperazinyl]benzenamine (5.7 g, 22.4 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 (4 g, 22.5 mmol) (Aldrich) in N,N-dimethylformamide (40 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 hr. then poured into ice-water (1500 mL), stirred for 30 min. then the precipitate filtered and washed with water and dried under vacuum to give 4-cyclopentyl-1-(4-isothiocyanatophenyl)piperazine (6 g, 93%)

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 hr
  4. additionthen poured into ice-water (1500 mL)
  5. stirringstirred for 30 min.
  6. filtrationthe precipitate filtered
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-01b80e98a8b94493a299a24fe1a57912
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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