Ethylamine → N-ethyl-6,6-dimethyl-2,4-heptadiynylamine hydrochloride

Participants

Reaction Steps

A methanol solution (7.5 ml) of 0.75 ml of propargyl bromide was added dropwise to 6 ml of a 70% aqueous solution of ethylamine with stirring and ice cooling, and the mixture was stirred for 1.5 hours. 120 mg of copper(I) chloride and 100 mg of hydroxylamine hydrochloride were added, and to this solution, a methanol solution(3 ml) of 5.6 mg of 1-bromo-3,3-dimethyl-1-butyne [synthesized by a bromination of lithiated tert-butylacetylene with bromine ] was added dropwise under ice cooling. The mixture was stirred at room temperature for 2 hours, and then the solvent was evaporated. The residue was worked up in a customary manner, and the product was treated with a methanol solution of hydrogen chloride to give 0.94 g of the captioned hydrochloride as a white crystalline powder.

Provenance & Evidence