Triethylamine → n-(2,2-Dimethoxyethyl)-2-(3-methoxyphenyl)acetamide

Participants

Reaction Steps

A solution of (3-methoxy-phenyl)-acetyl chloride (40 g, 0.22 mol) in chloroform (100 mL) was added dropwise to a solution of 2,2-dimethoxy-ethylamine (25 mL, 0.23 mol) and triethylamine (34 mL, 1.1 eq) in chloroform (400 mL) at 0° C., and then the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aqueous 1N HCl, and then again with water, dried (MgSO4), filtered and concentrated to provide N-(2,2-dimethoxy-ethyl)-2-(3-methoxy-phenyl)-acetamide (53.8 g, 98%). 1H-NMR (CDCl3) δ 7.27 (t, J=8.8 Hz, 1H), 6.84 (s, 1H), 6.81 (d, J=8.8 Hz, 2H), 5.66 (br s, 1H), 4.31 (t, J=5.2 Hz, 1H), 3.80 (s, 3H), 3.54 (s, 2H), 3.35 (t, J=5.2 Hz, 2H), 3.33 (s, 6H); LC/MS (ESI+): 222.15 [(M−MeOH)+H].

Provenance & Evidence