4-(4-Oxopiperidin-1-yl)benzonitrile → 4-(4-Benzyl-4-hydroxy-1-piperidinyl)benzonitrile

Participants

Reaction Steps

A solution of benzylmagnesium chloride (1.90 mL of a 2M solution in THF, 3.80 mmol) at −78° C. was treated with 4-(4-oxo-1-piperidinyl)benzonitrile (prepared according to the procedure described in Synthesis 1981, 606-608, 0.30 g, 1.51 mmol), and was allowed to warm to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 20% ethyl acetate in hexanes to give the desired product (0.087 g, 20%). MS (ESI) m/e 293 (M+H)+.

Provenance & Evidence