Dimethylamine → 4-[2-(Dimethylamino)-2-oxoethyl]benzeneacetic acid

Participants

Reaction Steps

N,N'-Carbonyldiimidazole (11.4 g) was added to a stirred solution of 1,4-phenylenediacetic acid (11.4 g) in dry dimethylformamide (300 ml) under an atmosphere of nitrogen. The mixture was stirred at 20° for 2 h as dimethylamine gas (about 10 g) was bubbled through. The reaction mixture was then stirred at 20° for 3 h and evaporated in vacuo to leave a brown oil which was diluted with saturated K2CO3 solution (50 ml). The resulting mixture was evaporated in vacuo to leave an off-white solid which was triturated with EA (2×200 ml). The organic phase was discarded and the aqueous phase was acidified (pH1) with 5M hydrochloric acid to precipitate an off-white solid which was triturated with absolute ethanol (25 ml) and filtered to give the title compound (1.1 g) as a fine white solid m.p. 163°-165° (softening at 160°).

Provenance & Evidence