Water → HCID 54352100, compound

Participants

Reaction Conditions

Reaction Steps

To 112.31 g (0.504 mol) of (S)-N-(1-chloro-2-propyl)-N-cyanomethylbenzylamine or the the mixture of compounds from step 1c, in 500 mL of anhdrous DMSO under nitrogen atmosphere was added 37.10 g (0.757 mol) of sodium cyanide. The reaction was stirred at 60° C. for 21 hours, slurried with water and extracted with ether. The extract was washed with brine, dried over magnesium sulfate, concentrated, and the residue chromatographed on silica gel, eluting with ethyl acetate:hexane in 1:4, 1:2, and 1:1 ratios to give 81.47 g (75.5% yield) of the title compound. MS M/Z: 231, 233 (M+NH4). NMR (CDCl3) δ: 1.41 (3H, d, J=6.5 Hz), 2.57 (1H, dd, J=6.5, J=16.5 Hz), 2.66 (1H, dd, J=6.5, J=16.5 Hz), 3.34 (1H, sextet, J=6.5 Hz), 3.48 (2H, s), 3.81 (2H, s), 7.36 (5H, m).

Provenance & Evidence