Dimethylamine → n,n-Dimethyl-2-(4-nitrophenyl)ethanamine

Participants

Reaction Steps

A pressure tube was charged with 1-(2-bromoethyl)-4-nitrobenzene (1 g, 4.35 mmol) in acetonitrile (5 mL). Triethylamine (2.4 mL) and dimethylamine, 2M in tetrahydrofuran (0.784 g, 17.39 mmol) were added, and the sealed tube was stirred at ambient temperature for 2 days. The reaction mixture was partitioned between dilute NaHCO3 solution and ethyl acetate, then extracted another two times with ethyl acetate. The product was then extracted into 2N HCl (2×25 mL). Following neutralization with 2N NaOH, the aqueous mixture was extracted with ethyl acetate (3×). The extracts were dried (Na2SO4), filtered and concentrated to give the title compound. MS (ESI(+)) m/e 194.9 (M+H)+.

Provenance & Evidence