Diisopropylethylamine → 4-(3-(4-(trifluoromethyl)phenoxy)benzylidene)-N-(3,4-dimethylisoxazol-5-yl)piperidine-1-carboxamide

Participants

Reaction Steps

4-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride (200 mg, 0.541 mmol, from Example 53, Step 5), phenyl 3,4-dimethylisoxazol-5-ylcarbamate (126 mg, 0.541 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 5-amino-3,4-dimethylisoxazole) and diisopropylethylamine (0.20 mL, 1.15 mmol) were combined in acetonitrile (5 mL) and stirred at room temperature. After 16 h, the reaction was concentrated and the residue was purified by silica gel chromatography (0-30% EtOAc:CH2Cl2) to afford the title compound (218 mg) as a white solid. MS APCI M+ 472.3, 431.2, 375.3, 334.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.83 (s, 3H) 2.18 (s, 3H) 2.44 (td, J=5.77, 1.07 Hz, 2H) 2.54 (td, J=5.81, 1.16 Hz, 2H) 3.49-3.54 (m, 2H) 3.59-3.63 (m, 2H) 6.44 (s, 1H) 6.90-6.98 (m, 2H) 7.05-7.14 (m, 3H) 7.35-7.44 (m, 1H) 7.59-7.67 (m, 2H).

Provenance & Evidence