1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-{[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]methyl}-3,3-diphenylpiperidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-4-fluoro-N-hydroxybenzimidamide (0.025 g, 0.162 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.050 g, 0.162 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.046 g, 0.242 mmol) was stirred in 1,2-dichloroethane (0.5 mL) at room temperature. After stirring for 1 hour, the reaction was heated to 85° C. and stirred overnight. The reaction was cooled, loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.09-8.15 (m, 2H), 7.24-7.34 (m, 10H), 7.16-7.24 (m, 2H), 4.91 (s, 2H), 3.62 (t, J=6.4 Hz, 2H), 2.68-2.73 (m, 2H), 1.87-1.96 (m, 2H); MS (ESI+) m/z 428 (M+H)+.

Provenance & Evidence