Sodium borohydride → 1-Benzyl-3-cyano-4-hydroxypiperidine

Participants

Reaction Steps

Sodium borohydride (0.89 g, 23.37 mmole) was added to the stirred solution of 1-benzyl-3-cyanopiperidin-4-one (2.5 g, 11.68 mmole) in ethanol (125 ml) at 0° C. over a period of 30 min, and stirring was continued for 2 hr at 5° C. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with ethyl acetate. The extract was concentrated to dryness to furnish 1-benzyl-3-cyano-4-hydroxypiperidine product as oil. Yield 1.85 g (73%) C13H16N2O, m/z 217 (M+1), PMR (CDCl3): 1.78 (2H, m, H5), 2.22 (1H, m, H3), 2.6-3.12 (4H, m, H2 & H6), 3.58 (1H, m, H4), 3.65 (2H, s, CH2—Ar), 7.32 (5H, s, ArH).

Provenance & Evidence