N-Methylaniline → N-methyl-N-(prop-2-yn-1-yl)aniline

Participants

Reaction Conditions

Reaction Steps

34 ml of a 2.7M solution of n-butyllithium in n-heptane are added dropwise at room temperature under nitrogen in the course of 1 hour to a solution of 10 g (93 mmol) of N-methylaniline in 100 ml of absolute ether. The temperature increases to reflux of the reaction mass. After 1 hour's reflux, the yellow solution is cooled to −10° C. and then in the course of 30 minutes a solution of 11.3 g (102 mmol) of propargyl bromide in toluene is added dropwise. The mixture is then stirred at room temperature for 8 hours. After customary aqueous working-up, the product of formula (101a) is purified by distillation. A yellow oil is obtained.

Provenance & Evidence