4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]pyridine → 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]piperidine

Participants

Reaction Steps

4-[2-(2,3-dimethoxyphenyl)-1-hydroxyethyl]pyridine (20.0 g, 0.077 mol) in acetic acid (170 ml) over 1.5 g of PtO2 was hydrogenated for 45 minutes on a Parr shaker. The reaction was filtered through Celite and filtrate combined with another run of 21.0 g (0.08 mol). The combined filtrates were concentrated in vacuo and the resulting oil was diluted with water. The aqueous solution was made basic with 50% aqueous NaOH, and the basic mixture extracted with EtOAc. The organic extract was washed with water, dried (magnesium sulfate) and then concentrated to afford 34.3 g of an oil that solidified upon standing. The solid was removed and recrystallized twice from isopropyl ether at 5° C. to afford the piperidine as a white solid, mp 82-84° C.

Provenance & Evidence