Water → Tert-butyl 4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]piperazine-1-carboxylate

HRID 1352360Notes

Reaction equation

HRID 1352360 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[S:3][C:4]([C:7]([F:10])([F:9])[F:8])=[N:5][N:6]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole

Product 1

HCID 68407744Tert-butyl 4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.2 mmol 2-bromo-5-trifluoromethyl-[1,3,4]thiadiazole (CA 37461-6-3; prepared according to DE2533605), 2.3 mmol piperazine-1-carboxylic acid tert-butyl ester and 4.3 mmol potassium carbonate in 10 ml acetonitrile was refluxed for 4 hours. The reaction mixture was cooled, poured into water and extracted 3 times with ethyl acetate. Concentration and recrystallisation of the crude material from diethyl ether yielded the title compound as a colorless solid. MS (m/e): 397.2 ([M+CH3COO]31 , 100%).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted 3 times with ethyl acetate
  4. concentrationConcentration and recrystallisation of the crude material from diethyl ether

Sources & evidence

ORD record
ord-fcafa14ec0de4d25be1763a4ce860165
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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