Ethanol → 4-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide

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Reaction Conditions

Reaction Steps

Alternately, combine 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride (20.3 g, 58 mmol), a concentrated aqueous sodium hydroxide solution (20 mL, 50%) and ethanol (400 mL). Heat to about 50° C. Add an aqueous solution of hydrogen peroxide (40 mL, 30%) over about 10 minutes. After 18 hours, add an aqueous solution of hydrogen peroxide (10 mL). After 3 hour, cool to ambient temperature and dilute with water (200 mL), concentrate in vacuo to remove most to the ethanol (about 400 mL). Add water (200 mL) and extract twice with ethyl acetate. Extract the combined organic layers with water and then brine, dry over MgSO4, filter, and evaporate in vacuo to give a solid. Dissolve the residue in hot ethyl acetate (500 mL) by the addition of methanol. Filter and concentrate the filtrate in vacuo to give a solid. Triturate the solid with dichloromethane and collect by filtration, and dry to give 1-benzyl-(4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide: Rf =0.62 (silica gel, 7/3 dichloromethane/methanol).

Provenance & Evidence