alpha,alpha-Bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol → alpha,alpha-Bis(4-methoxyphenyl)-4-piperidinemethanol

Participants

Reaction Steps

A solution of 36.7 g (0.088 mole) of α,α-bis(4-methoxyphenyl)-1-(phenylmethyl)-4-piperidinemethanol in 500 ml of absolute ethanol was hydrogenated over 1 tsp of 5% Pd/C at 60° C. in a Parr apparatus over the weekend. The mixture was cooled, filtered through Celite®, fresh catalyst added to the filtrate and the process repeated until no starting material was present by mass spectral analysis. The filtrate was concentrated and the residue was partitioned between methylene chloride and a 5% sodium hydroxide solution. The organic layer was dried over sodium sulfate and concentrated to give a solid residue. The solid was recrystallized from 2-propanol to yield 8.6 g (30%) of white solid, mp 153°-155° C.

Provenance & Evidence