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

HRID 2191143Notes

Reaction equation

HRID 2191143 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14](=O)[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[N:25][OH:26])[CH3:15])[C@@H:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 594381311-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone

Product 1

HCID 866440181-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone oximeYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 g (6.1 mmol) 1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone, 0.869 g (12.5 mmol) hydroxylamine, hydrochloride and 1.03 g (12.5 mmol) sodium acetate in 25 mL ethanol was heated to reflux for 2 h. After cooling to room temperature water was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a ethyl acetate. The product containing fractions were evaporated to yield 1.6 g (77%) of the title compound as colorless viscous oil. MS (m/e): 343.2 [(M+H)+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography on silica eluting with a ethyl acetate
  9. additionThe product containing fractions
  10. customwere evaporated

Sources & evidence

ORD record
ord-6cb2a17c345c4adbba99d9ee92b55d06
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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