Azacyclonol → 1-(2-{4-[Hydroxy(diphenyl)methyl]piperidin-1-yl}-2-oxoethyl)-3,3-diphenylpiperidin-2-one

Participants

Reaction Steps

To a solution of diphenyl(piperidin-4-yl)methanol (0.13 g, 0.5 mmol) in dichloromethane (10 mL) under nitrogen was added 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.16 g, 0.50 mmol) followed by N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.19 g, 1.00 mmol) and N,N-dimethylpyridin-4-amine (6 mg, 0.05 mmol). The reaction mixture was stirred overnight at room temperature. The reaction was concentrated and the residue was partitioned in ethyl acetate/water (8:2, 400 mL). The organic layer was washed with water followed by brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:3) gave the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.42-7.48 (m, 4H), 7.16-7.35 (m, 16H), 4.63-4.71 (m, 1H), 4.20 (d, J=1.5 Hz, 2H), 3.77-3.84 (m, 1H), 3.42-3.54 (m, 2H), 2.97-3.06 (m, 1H), 2.57-2.68 (m, 4H), 1.74-1.87 (m, 2H), 1.46-1.64 (m, 3H), 1.29-1.42 (m, 2H); MS (ESI+) m/z 559 (M+H)+.

Provenance & Evidence