Cyclopentanone → 1-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

Participants

Reaction Steps

To an ice-cooled suspension of dibenzylamine hydrochloride (13.5 g; 0.058 mol) and cyclopentanone (4.86 g; 0.058 mol) in 25% ethanol in water (100 ml) was added ethanol (60 ml) and a solution of potassium cyanide (3.78 g; 0.058 mol) in water (35 ml) dropwise over 20 minutes with stirring. After 6 days the reaction mixture was extracted with ethyl acetate, washed with sodium bicarbonate solution, dried (Na2SO4) and evaporated in vacuo to afford the title compound as an off white solid (8.32 g, 49%). 1H NMR (CDCl3) δ: 1.72 (6H, m), 2.12 (2H, m), 3.78 (4H, m), 7.1-7.3 (10H, m); Mass Spectrum (Electrospray LC/MS): Found 264 (MH+−HCN). C20H22N2 requires 290. Ret. time 1.88 min.

Provenance & Evidence