Propanal → HCID 18353217, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[2-(4-methoxyphenyl)-1-methylethyl]-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine (0.87 grams, 2.4 mmole), propionaldehyde (0.2 ml, 2.5 mmole) and sodium triacetoxyborohydride (0.763 grams, 3.6 mmole) in 1,2-dichloroethane (25 ml) was stirred at 22° C. for 16 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between 100 ml ethyl ether and 25 ml 10% aqueous sodium carbonate. The dried (anhydrous magnesium sulfate) and concentrated organic phase was subjected to flash chromatography over silica gel 230-400 mesh eluting with 10% ethyl acetate/hexane. Product fractions were concentrated under reduced pressure to give N-[2-(4-methoxyphenyl)-1-methylethyl]-N-propyl-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)amine as a syrup (0.93 grams, 95%), M+H 405.

Provenance & Evidence