2,2,2,4'-Tetrafluoroacetophenone → HCID 66583043, compound

HRID 1972431Notes

Reaction equation

HRID 1972431 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].CCN(C(C)C)C(C)C.Cl.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)(=[O:31])=[O:30]>C(#N)C>[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:35]2[CH2:36][CH2:37][N:32]([S:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)(=[O:31])=[O:30])[CH2:33][CH2:34]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 81531DiisopropylethylamineHCID 467434531032757-93-9

Product 1

HCID 66583043HCID 66583043, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

2,2,2-trifluoro-1-(4-fluorophenyl)ethanone (2.6 g, 13 mmol, Sigma-Aldrich, St. Louis, Mo.), Hünig's base (5.8 mL, 34 mmol), 1-(2-thiophenylsulfonyl)piperazine hydrochloride (3.0 g, 11 mmol, Example 29, step 1), and acetonitrile (22 mL) was added to a high-pressure reaction vessel. The vessel was sealed and heated at 110° C. for 19 h. After cooling to room temperature, the mixture was partitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (50 mL) and the layers were separated. The organic material was washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried (Na2SO4) and filtered. The filtrate was concentrated, hexanes (100 mL) was added to the residue and the slurry was filtered to give 2,2,2-trifluoro-1-(4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)ethanone (2.5 g) as a light tan solid. The material was used in the next step without purification

Workup

  1. customThe vessel was sealed
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was partitioned between EtOAc (100 mL) and saturated aqueous sodium bicarbonate (50 mL)
  4. customthe layers were separated
  5. washThe organic material was washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. additionhexanes (100 mL) was added to the residue
  10. filtrationthe slurry was filtered

Sources & evidence

ORD record
ord-536f146574c1499f84f212b9c52c3d4c
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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