Dimethylamine → 3-Methoxy-N,N-dimethylbenzylamine

Participants

Reaction Steps

Four hundred grams of dimethylamine were added to 1.5 liters of acetonitrile previously cooled with an external ice/ethanol bath. To this solution were added 322.7 g. of 3-methoxybenzyl chloride in a dropwise fashion. When the addition was completed, the reaction was stirred for an additional four hours with cooling. The reaction was stirred an additional 20 hours at room temperature, heated to reflux for five hours, and then concentrated under reduced pressure. The residue was taken up in water, the aqueous solution was made strongly basic with aqueous sodium hydroxide, and the solution was then extracted with diethyl ether. The ether layer was first washed with water and then extracted with dilute hydrochloric acid. The acid layer was made basic with an aqueous sodium hydroxide solution and extracted with diethyl ether. The layer was dried over sodium sulfate and evaporated to dryness. The residue was vacuum distilled at 3 torr. The fraction between 88 and 92° C. afforded 257 g. of the desired title intermediate. NMR.

Provenance & Evidence