1-Methyl-4-(pyridin-2-yl)piperidine-4-carbonitrile → (1-Methyl-4-(pyridin-2-yl)piperidin-4-yl)methanamine

Participants

Reaction Steps

A solution of 1-methyl-4-(pyridin-2-yl)piperidine-4-carbonitrile (0.544 g, 2.70 mmol) in tetrahydrofuran (10 mL) was slowly added to a suspension of lithium aluminum hydride (0.205 g, 5.41 mmol) in tetrahydrofuran (10 mL) at 23° C. The reaction was stirred overnight, then quenched with sodium sulfate decehydrate. This was stirred for 1 hour, then ethyl acetate was added and the slurry was stirred for 2 more hours. Celite was added and the paste was filtered on Celite. The filtrate was concentrated to afford an oil (0.518 g, 93%) which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 1.76-1.88 (2H, m), 2.07-2.19 (2H, m), 2.23 (3H, s), 2.43 (2H, br d, J=14.6 Hz), 2.58-2.69 (2H, m), 2.87 (2H, s), 7.16 (1H, ddd, J=7.52, 4.86 and 1.01 Hz), 7.33 (1H, d, J=8.08 Hz), 7.69 (1H, td, J=7.77 and 1.89 Hz), 8.65 (1H, d, J=4.80 and 1.01 Hz).

Provenance & Evidence