Pentane → 3-(Phenyl(4-(trifluoromethyl)phenyl)methylene)piperidine

Participants

Reaction Steps

To a solution of phenyl(4-(trifluoromethyl)phenyl)methanone (1.5 g, 6.0 mmol) and tert-butyl 3-oxopiperidine-1-carboxylate (1.3 g, 6.5 mmol) in THF (20 mL) was added Zn (1.8 g, 28.5 mmol) and the resulting mixture was stirred at rt for 10 min and was then cooled to 0° C. To this was added TiCl4 (1.4 mL, 13.5 mmol) dropwise. The reaction mixture was stirred first at rt for 15 min and then at 50° C. for 4 h. The solvent was removed under vacuum. Then it was cooled to 0-5° C. and added 2N HCl solution and extracted with ethyl acetate. The combined organic layer was washed with K2CO3 solution, dried over anhydrous sodium sulfate and concentrated under vacuum to afford the crude product. It was cooled to 0-5° C., pentane was added and stirred for 30 min and dried under vacuum to afford 3-(phenyl(4-(trifluoromethyl)phenyl)methylene)piperidine (1.1 g, 57% yield) as a grey solid. MS (ESI, pos. ion) m/z: 318 (M+1).

Provenance & Evidence