Sodium Carbonate → N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl]amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-[2-(4-methoxyphenyl)-1-methylethyl]ethylamine hydrochloride (2.0 grams, 8.71 mole) and sodium carbonate (3.2 grams, 30 mole) in toluene (75 ml) and water (50 ml) was added dropwise to a solution of 1-benzyloxycarbonylpiperidine-4-carbonyl chloride (2.67 grams, 9.5 mmole) in toluene (25 ml). The reaction mixture was stirred at 22° C. for 16 hours.The mixture was diluted with ethyl acetate (100 ml), the organic phase was dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to flash column chromatography over silica gel eluting with 30% ethyl acetate in hexane. The N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl]amine was obtained as an oil, (3.5 grams, 95%), M+H 439.

Provenance & Evidence