Cornforth reagent → 1-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone

HRID 1840755Notes

Reaction equation

[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH:34]([OH:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridinium dichromate (4.0 g, 10.63 mmol) was added to a solution of 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol (0.5 g, 1.5 mmol) in dimethylformamide (25 ml) at 0° C. The resulting solution was stirred at 0° C. until the starting material was consumed and then quenched with water, basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over sodium sulfate. The residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes to give 1-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone (0.32 g) as an oil.

Workup

customwas consumed
customquenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
customThe residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes

Sources & evidence

ORD record: ord-22df506c29594a8c887071cd94f1f725
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683074B1

Reaction notes

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