Acetonitrile → 2,2,2-Trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanone

HRID 1972353Notes

Reaction equation

HRID 1972353 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)=[O:4].Cl.[C:15]1([S:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC#N.C(N(CC)CC)C>CCOC(C)=O.O.CCCCCC>[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:27]2[CH2:28][CH2:29][N:24]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[CH2:25][CH2:26]2)=[CH:7][CH:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 27565811-(Benzenesulfonyl)piperazine hydrochloride

Product 1

HCID 665823572,2,2-Trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanoneYield 50.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 125 ml, pressure tube was charged with 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone (7.31 g, 38.1 mmol, Sigma-Aldrich, St. Louis, Mo.), 1-(phenylsulfonyl)piperazine hydrochloride (5.00 g, 19.0 mmol), 20 mL of CH3CN, and triethylamine (7.96 mL, 57.1 mmol). The tube was sealed and heated at 110° C. for 3 h. After that time, the mixture was diluted with EtOAc (100 mL) and water (50 mL). The organics were separated, dried (MgSO4) and concentrated to give a white solid. This solid was slurried with hexane (150 mL) to give 2,2,2-trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanone (3.85 g) as a bright white solid.

Workup

  1. customThe tube was sealed
  2. customThe organics were separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a white solid

Sources & evidence

ORD record
ord-e46e3af9d2f84f04901fd03ab92c2018
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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