Ethanol → Napactadine Hydrochloride
Reaction equation
[ClH:1].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][C:13](=[NH:17])OCC.[CH3:18][NH2:19].[CH2:20](O)C>>[ClH:1].[CH3:18][NH:19][C:13](=[N:17][CH3:20])[CH2:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1Participants
4
Conditions
- Temperature
- 2 °C
Procedure
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.