1,1'-Thiocarbonyldiimidazole → 1-(4-Isothiocyanatophenyl)-4-cyclopropylmethylpiperazine

HRID 10796Notes

Reaction equation

HRID 10796 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[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]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:6][CH2:7]2)=[CH:16][CH:15]=1)=[C:18]=[S:19]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 219589114-[4-(Cyclopropylmethyl)piperazin-1-yl]aniline

Product 1

HCID 219589161-(4-Isothiocyanatophenyl)-4-cyclopropylmethylpiperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 4-[4-(cyclopropylmethyl)-1-piperazinyl]benzenamine (3.7 g, 16 mmol) (from Step B above) in N,N-dimethylformamide (50 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (2.87 g, 16.1 mmol) (Aldrich) in N,N-dimethylformamide (25 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 (1000 mL) was added and the mixture was stirred for 30 min. The solid was filtered off and washed with water and dried under vacuum. (4 g, 91%).

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 h
  4. additionIce-water (1000 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-604b53f6ab9a40748ebb4ec414303e96
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Reaction notes

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