1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oxime → 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamine

HRID 2191144Notes

Reaction equation

HRID 2191144 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[N:16]O)[CH3:15])[C@@H:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([CH:14]([NH2:16])[CH3:15])[C@@H:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 866440181-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oxime

Product 1

HCID 594381231-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.6 g (4.7 mmol) 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oxime in 300 mL methanol was hydrogenated over Raney Nickel (3.5 bar, 30° C., 23 h). The mixture was filtered and evaporated to dryness. The residue was purified by column chromatography over silica eluting with a gradient formed from DCM, methanol and NH3aq. to yield after evaporation of the product containing fractions 0.7 g (45%) of the title compound as colorless viscous oil. MS (m/e): 329.4 [(M+H)+].

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography over silica eluting with a gradient
  4. customformed from DCM, methanol and NH3aq
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 0.7 g (45%) of the title compound as colorless viscous oil

Sources & evidence

ORD record
ord-c5ec713563cb4339be7f1795b7f073c7
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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