4-Hydroxy-4-phenyl-1-(piperidin-1-yl)butan-1-one → HCID 558699, compound

HRID 429182Notes

Reaction equation

HRID 429182 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 185234994-Hydroxy-4-phenyl-1-(piperidin-1-yl)butan-1-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 558699HCID 558699, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-4-phenyl-1-piperidine-1-yl-butan-1-one (4.00 g, 16.2 mmol), prepared in the previous step, and pyridinium chlorochromate (5.23 g, 24.3 mmol) in 150 ml of methylene chloride was stirred at room temperature for 2.25 hours. The reaction was poured onto 400 g of silica gel (230-400 mesh) and the material eluted with methylene chloride-ethyl acetate. Isolation of the major component gave 4-oxo-4-phenyl-1-piperidine-1-yl-butan-1-one (3.66 g, 92%) as a green solid. Recrystallization of a portion of this solid from ethyl acetate-hexane gave an analytically pure sample, mp 52-54° C.

Workup

  1. additionThe reaction was poured onto 400 g of silica gel (230-400 mesh)
  2. washthe material eluted with methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-2c5fde81b68e4932b71ff056fa2f52a2
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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