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

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-4-chloro-N-hydroxybenzimidamide (0.121 g, 0.711 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.200 g, 0.646 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.161 g, 0.840 mmol) were stirred together in dichloroethane (0.5 mL) at room temperature for 2 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF15-12 column (Analogix®) and the product eluted using a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate over 20 minutes (Flow=30 mL/minute) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.09-8.02 (m, 2H), 7.52-7.45 (m, 2H), 7.33-7.25 (m, 10H), 4.91 (s, 2H), 3.62 (t, J=6.5, 2H), 2.73-2.67 (m, 2H), 1.98-1.85 (m, 2H); MS (ESI+) m/z 444.0 (M+H)+.

Provenance & Evidence