Dimethylamine → N-(2-dimethylamino-butyryl)-2,6-dimethyl-aniline

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Reaction Steps

A mixture of 7.7 g (28.5 mmoles) of N-(2-bromo-butyryl)-2,6-dimethyl-aniline, 70 ml of ethanol and 20 ml of a 33% aqueous dimethyl amine solution is heated in a bomb at 100°-110° C. for 6 hours. The mixture is cooled, diluted with 150 ml of diethyl ether and 40 ml of water, the phases are separated, and the aqueous phase is extracted twice with 25 ml of diethyl ether, each. The etheral solutions are combined, washed thrice with 35 ml of 1 n aqueous hydrochloric acid, each, the aqueous acidic solutions are combined, rendered alkaline (pH=9) with concentrated aqueous ammonia, and extracted thrice with 40 ml of 1,2-dichloroethane, each. The dichloroethane solutions are combined, washed thrice with 20 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The oily residue, weighing 7.1 g, is triturated with diisopropyl ether to obtain 4.1 g of crude product, which is recrystallized then from ethyl acetate. 3.2 g (47.9%) of pure N-(2-dimethylamino-butyryl)-2,6-dimethyl-aniline are obtained; m.p.: 155°-157° C.

Provenance & Evidence