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

HRID 10777

Reaction equation

HRID 10777 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH3:3].[C:17](N1C=CN=C1)(N1C=CN=C1)=[S:18]>CN(C)C=O>[N:16]([C:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH2:8][CH2:9][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6]2)=[CH:11][CH:12]=1)=[C:17]=[S:18]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]aniline

Product 1

HCID 98783861-(4-Isothiocyanatophenyl)-4-(1-methylethyl)piperazineYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 4-[4-(1-methylethyl)-1-piperazinyl]benzenamine (1.6 g,˜6.8 mmol) (from Step B above) in N,N-dimethylformamide (25 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (1.4 g, 7.7 mmol) (Aldrich) in N,N-dimethylformamide (30 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 was added and the mixture was extracted with ether. The ether layer was dried (MgSO4), filtered, and evaporated to give 1-(4-isothiocyanatophenyl)-4-(1-methylethyl)piperazine (1.8 g, quantitative yield).

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred for 1 h
  4. additionIce-water was added
  5. extractionthe mixture was extracted with ether
  6. dry with materialThe ether layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9f2a80a91dcc4887a781077f3e4406f3
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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