Acetaldehyde → Benzyl-N-(1-cyanoethyl)glycine hydrochloride

Participants

Reaction Steps

Trimethylsilyl cyanide (TMSCN) (4.0 mL, 30 mmol) was added cautiously to a stirred solution of benzyl glycine free base (5.0 g, 30 mmol) and acetaldehyde (1.7 mL, 30 mmol) in methylene chloride (15 mL) under argon atmosphere. After 15 h, the volatile components were removed in vacuo, and the residue was dissolved in ethyl acetate (200 mL), washed with brine (100 mL), dried (Na2SO4) and evaporated to an oil. The oil was redissolved in ether (30 mL) and ethanol (30 mL), and 1M HCl in ether (33 mL) was added dropwise to give the title compound (6.60 g, 100%) as an off-white crystalline precipitate. mp: 137-138° C.; 1H-NMR (300 MHz, CD3OD) δ 7.31-7.48 (m, 5H), 5.32 (s, 2H), 4.68 (q, J=7.0 Hz, 1H), 4.22 (s, 2H), 1.73 (d, J=7.1 Hz, 3H); CI MS m/z=192 (M+H). Anal. Calcd. for C12H14N2O2. HCl: C, 56.49; H, 5.95; N, 11.00. Found: C, 56.32; H, 5.88, N, 10.89.

Provenance & Evidence