Water → Tert-butyl [(3-cyanobenzyl)(methyl)amino]acetate

Participants

Reaction Steps

To a stirred solution of sarcosine tert-butyl ester hydrochloride (8.1 g, 44.9 mmol) and triethylamine (17 mL, 122.4 mmol) in acetonitrile (100 mL) under N2, was added 3-(bromomethyl)benzonitrile (8 g, 40.8 mmol) portionwise over a period of 10 min at 0° C. After being stirred at RT for 3 h, the reaction mixture was poured into water and extracted with DCM. Then the organic layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a pale green liquid (9 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 7.71-7.72 (2H, m), 7.63-7.65 (1H, m), 7.53-7.55 (1H, m), 3.66 (2H, s), 3.18 (2H, s), 2.22 (3H, s), 1.41 (9H, s).

Provenance & Evidence