Potassium Carbonate → HCID 67442456, compound

Participants

Reaction Steps

329 mg of tert-butyl (3S)-piperidin-3-ylcarbamate and 189 mg of potassium carbonate were added to a solution of 400 mg of 1-(chloroacetyl)-4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine in 10 ml of acetonitrile, followed by heating under reflux for 2 hours. After the reaction mixture was concentrated under reduced pressure, chloroform and saturated aqueous sodium hydrogencarbonate solution were added to the residue, then the organic layer was fractionated. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water). The obtained oil was dissolved in 10 ml of ethanol, and 10 ml of 4N hydrochloric acid-ethyl acetate was added to the solution, followed by stirring at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was crystallized from 2-propanol-diisopropyl ether. The crystals were recrystallized from water-ethanol to give 473 mg of (3S)-1-(2-{4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidin-1-yl}-2-oxoethyl)piperidine-3-amine dihydrochloride.

Provenance & Evidence