5-(3,4-Dichlorophenyl)-5-[3-(tetrahydropyran-4-yloxy)-propyl]-2-piperidone → 3-(3,4-Dichlorophenyl)-3-[3-(tetrahydropyran-4-yloxy)-propyl]-piperidine

Participants

Reaction Conditions

Reaction Steps

Piperidone (6) (42.9 g, 0.111 mol) in dry THF (300 mL) was added to a suspension of LAH (8.4 g, 0.222 mol) in dry THF (500 mL), which was then heated under N2 at 60° C. in an oil bath for 5 hours, then cooled and stirred at room temperature overnight (20 hours). The reaction was quenched by H2O (8.5 mL), 4N NaOH (8.5 mL), and H2O (0.5 mL), respectively. White solid was filtered and washed with Et2O. The filtrate was concentrated, and the crude oil was purified by flash chromatography (CH2Cl2—MeOH/95:5) to give a colorless oil (37.94 g 91.8%).

Provenance & Evidence