benzyldimethyl(2-phenoxyethyl)ammonium

Originator

Alcopar,Wellcome,UK,1960

Definition

ChEBI: Bephenium is an aromatic amine.

Manufacturing Process

First, dimethylamino-2-phenoxyethanewas made by reacting chloro-2- phenoxyethane with dimethylamine. Benzyl chloride (10 grams) was then added to a solution of 1-dimethylamino-2-phenoxyethane (12.3 grams) in acetone (35 ml). The mixture warmed spontaneously and N-benzyl-N,Ndimethyl-N-2-phenoxyethylammonium chloride slowly crystallized. After 24 hours, this solid was filtered off, washed with fresh acetone and dried immediately in vacuo, MP 135°-136°C.
2-Hydroxy-3-naphthoic acid (1.88 grams) was dissolved in hot aqueous sodium hydroxide (0.5N; 20 ml) and the resulting solution was slowly added to a solution of N-benzyl-N,N-dimethyl-N-2-phenoxyethylammonium chloride (2.9 grams) in water (5 ml). A gum separated at first but it solidified on scratching. After the addition was complete, the mixture was allowed to stand at room temperature for 2 hours and then filtered. The residue was washed with water and dried in vacuo to give N-benzyl-N,N-dimethyl-N-2- phenoxyethylammonium 2-hydroxy-3-naphthoate, MP 170°-171°C.

Therapeutic Function

Anthelmintic