Ethanol → Napactadine Hydrochloride

Participants

Reaction Conditions

Reaction Steps

In a 100 ml. reaction vessel, equipped with a stirrer, thermometer, a pressure-equalizing addition funnel, and a reflux condenser fitted with a drying tube, 11.95 grams (0.048 mol.) of ethyl 2-naphthaleneethanimidate hydrochloride was placed. A solution of 21.20 grams (0.683 mol.) of methylamine in 35 ml. of absolute ethanol was rapidly added to the reaction mixture. The temperature quickly rose to 65° C. and dropped to about 30° C. after all of the solution was added. The reaction mixture was kept between about 50°-53° C. for 21 hours. The reaction mixture was cooled to 2° C. and the white crystalline product was filtered off. The product was washed with toluene and dried to give 10.2 grams (85% yield) of the title compound. The crude product was recrystallized from absolute ethanol to yield 8.97 grams of the title compound. The melting point was 225.5°-227° C.

Provenance & Evidence