2-[trans-4-aminocyclohexyl]acetonitrile hydrochloride

1313279-47-8

1313279-48-9

The general procedure for the synthesis of 2-(trans-4-aminocyclohexyl)acetonitrile hydrochloride from tert-butyl (trans-4-(cyanomethyl)cyclohexyl)carbamate was as follows: to a 1L round bottom flask was added tert-butyl N-[(1r,4r)-4-(cyanomethyl)cyclohexyl]carbamate (620 g, 2.60 mol, 1.00 equiv) and 1,4-dioxane (2L). With stirring at 10 °C, a 1,4-dioxane solution of HCl (5 L, 4 M) was added slowly and dropwise. The reaction mixture was stirred at 25°C overnight. This reaction process was repeated 4 times and all reaction mixtures were combined. The solid product was collected by filtration and the solid was washed sequentially with 1,4-dioxane (3 × 3 L), ethyl acetate (3 × 3 L) and hexane (3 × 3 L). 2-[(1r,4r)-4-aminocyclohexyl]acetonitrile hydrochloride (1753 g, 96% yield) was finally obtained as a white solid. Mass spectrum (ESI): calculated value C8H14N2, 138.12; measured value m/z 139.25, [M+H]+. NMR hydrogen spectrum (300MHz, DMSO-d6): δ 8.14 (s, 3H), 2.96-2.84 (m, 1H), 2.46 (d, J=6.3Hz, 2H), 1.98 (d, J=11.1Hz, 2H), 1.79 (d, J=12.0Hz, 2H), 1.64-1.49 (m, 1H), 1.42 -1.29 (m, 2H), 1.18-1.04 (m, 2H).