Trifluoroacetic acid → 1-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

HRID 2066886Notes

Reaction equation

HRID 2066886 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][C:15](=[N:18][O:19][CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[CH2:14][CH2:13]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:23]1[CH2:24][CH2:25][CH:20]([O:19][N:18]=[C:15]2[CH2:16][CH2:17][N:12]([C:3]3[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=3[F:1])[CH2:13][CH2:14]2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49853805HCID 49853805, compound

Product 1

HCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oximeYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-1 (1.88 g, 4 mmol) in 30 mL of DCM, was added TFA (3 mL, 40 mmol) and the reaction mixture was stirred at room temperature for 3 h. It was quenched with saturated NaHCO3, extracted with DCM 3 times, dried and concentrated to give 1.37 g (3.7 mmol) of 63a.

Workup

  1. customIt was quenched with saturated NaHCO3
  2. extractionextracted with DCM 3 times
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c4e9ae6c9c62459484ced1d877a2741a
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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