Water → 1-(4-Trifluoromethanesulfonylphenyl)piperazine

HRID 2251189Notes

Reaction equation

HRID 2251189 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:12][C:11]([F:14])([F:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 3001141-Bromo-4-trifluoromethanesulfonylbenzene

Product 1

HCID 434552291-(4-Trifluoromethanesulfonylphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1 mmol 1-Bromo-4-trifluoromethanesulfonyl-benzene [Nodiff et al., J. Org. Chem. 25, 60 (1960)], 3 mmol of piperazine and 2 mmol of potassium carbonate in 5 ml of acetonitrile was refluxed for 2 hours. The resulting mixture was poured into water, extracted with ethyl acetate, dried, concentrated and purified by column chromatography (SiO2; Et2O/cyclohexane) to yield the title compound as a colorless solid. MS (m/e): 295.2 (MH+, 100%)

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography (SiO2; Et2O/cyclohexane)

Sources & evidence

ORD record
ord-261d611a34a14d9fb21ef95551b2344e
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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