4-Phenylpiperidin-4-ol → 4-(4-Hydroxy-4-phenylpiperidin-1-yl)naphthalene-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

1-Cyano-4-fluoronaphthalene (20 mg, 0.117 mmol) was dissolved in pyridine (1 mL). 4-Hydroxy-4-phenylpiperidine (83 mg, 0.467 mmol) was added and the reaction mixture was shaken at 110° C. for 3 days in a sealed vial. The reaction mixture was concentrated and re-suspended in 2 M HCl (1 mL). The product mixture was extracted with ethyl acetate (2×1 mL), and the combined organic phases were concentrated. The residue was purified by preparative reversed phase HPLC to give the title compound (14 mg, 36% yield) as a white solid.

Provenance & Evidence