1-Chloroethyl chloroformate → 2,2-Dimethylmorpholine hydrochloride

Participants

Reaction Steps

Dissolve 4-benzyl-2,2-dimethyl-morpholine (5.67 g, 27.6 mmol) in CH2Cl2 (50 mL) and add 1-chloroethyl chloroformate (4.60 mL, 42.2 mmol) while stirring at room temperature. After 4 h, concentrate the solution and treat the residue with MeOH (60 mL). Heat the mixture at 60° C. for 2 h, then concentrate again. Dissolve the residue in water (125 mL) and wash with tert-butyl methyl ether (125 mL). Concentrate the aqueous layer and dry the resulting residue at 80° C. under vacuum to give the title compound (3.91 g, 93%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.52 (2H, br s), 3.75 (2H, m), 2.89-2.96 (4H, m), 1.25 (6H, s).

Provenance & Evidence