3-Bromo-1,1,1-trifluoro-2-propanone → 1-[4-(Trifluoromethyl)-1,3-thiazol-2-yl]piperazine

HRID 1352340Notes

Reaction equation

HRID 1352340 reaction equation
[N:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:11][C:12](=O)[C:13]([F:16])([F:15])[F:14].CO.ClCCl>C(O)C>[F:14][C:13]([F:16])([F:15])[C:12]1[N:8]=[C:7]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[S:9][CH:11]=1

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 47396381-PiperazinecarbothioamideHCID 21226129Dichloromethane methanol

Product 1

HCID 137478101-[4-(Trifluoromethyl)-1,3-thiazol-2-yl]piperazineYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6.89 mmol 1-piperazinecarbothioamide in 10 ml ethanol was added 8.26 mmol 3-bromo-1,1,1-trifluoroacetone and the mixture was heated at 70° C. for 2 h. The mixture was then concentrated in vacuo and the residue resuspended in dichloromethane. Insoluble material was removed by filtration and the filtrate was concentrated in vacuo. Chromatography (SiO2, methanol/dichloromethane) afforded the title compound as a yellow crystalline solid (yield 41%). MS (m/e): 238.1 (M+H+, 100%).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customInsoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7264c8d9955e44a3bda935960628c153
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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