N'-Hydroxy-4-(trifluoromethyl)benzene-1-carboximidamide → 3,3-Diphenyl-1-({3-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}methyl)piperidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)—N-hydroxy-4-(trifluoromethyl)benzimidamide (0.033 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) were stirred together 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% ethyl acetate/hexane to 100% ethyl acetate over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 8.22-8.26 (m, 2H), 7.76-7.80 (m, 2H), 7.21-7.35 (m, 10H), 4.93 (s, 2H), 3.64 (t, J=6.4 Hz, 2H), 2.69-2.74 (m, 2H), 1.88-1.97 (m, 2H); MS (ESI+) m/z 478 (M+H)+.

Provenance & Evidence