Piperidine → 2-(Piperidin-1-ylmethyl)benzonitrile

Participants

Reaction Steps

A solution of 35 g (0.18 mole) of cyanobromotoluene and 16.18 g (0.19 mole) of piperidine in 300 mL of anhydrous DMF was treated with 73 g (0.5 mole) of K2CO3 at 50° C. for 2 hr. The reaction mixture was filtered through a plug of Celite, washed with 400 mL of ethyl acetate, and the filtrate was partitioned between ethyl acetate and ½ saturated brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, yielding 36 g (0.18 mole) 100% of 2-Piperidin-1-ylmethyl-benzonitrile. 1H NMR (300 MHz, CDCl3) 7.6 (m, 3H), 7.24 (m, 1H), 3.6 (s, 2H), 2.4 (m, 4H), 1.5 (m, 6H).

Provenance & Evidence