1-Benzyl-4-piperidone → HCID 53979967, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10.0 gm (44.8 mMol) 2-bromo-6-hydroxynaphthalene in tetrahydrofuran was added dropwise to a suspension of 9.42 gm (47.1 mMol) potassium hydride (20% suspension) in 180 mL tetrahydrofuran at 0° C. After stirring at this temperature for 2 hours the reaction mixture was cooled further to -78° C. and to it was added dropwise 58 mL (98.6 mMol) tert-butyllithium (1.7M in tetrahydrofuran). The mixture was stirred for 20 minutes at this temperature and then a solution of 8.73 mL (47.1 mMol) 1-benzyl-4-piperidone in 30 mL tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm gradually to room temperature and was stirred at this temperature for 18 hours. The reaction mixture was then partitioned between ethyl acetate and dilute ammonium hydroxide. The phases were separated and the aqueous phase was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 5% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 2.27 gm (15%) of the desired product.

Provenance & Evidence