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

Participants

Reaction Conditions

Reaction Steps

Combine 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride (1.6 g, 4.5 mmol), a concentrated aqueous sodium hydroxide solution (1.5 mL, 50%, 9 mmol) and ethanol (30 mL). Heat to about 55° C. Add an aqueous solution of hydrogen peroxide (3.0 mL, 30%, 26 mmol) over about 10 minutes. After 3 hours, add an aqueous solution of hydrogen peroxide (2.0 mL). After 1 hour, cool to ambient temperature and dilute with water (20 mL), concentrate in vacuo, add water (40 mL), and again concentrate in vacuo to give a solid. Collect the solid by filtration, rinse with water, and dry to give 1-benzyl-(4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide: Rf =0.20 (silica gel, 9/1 dichloromethane/methanol).

Provenance & Evidence