Asocainol (ASOC) belongs to class I antiarrhythmic drugs, i.e., those that exert their action at the level of sodium channels of the myocardial cell membrane.
A solution of a Grignard reagent is prepared from 5.5 g (0.23 mol) activated
magnesium turnings and 41.5 g (0.24 mol) phenethyl bromide in 200 ml
anhydrous diethyl ether. To this is added dropwise, at 35-40°C, a solution of
31.5 g (0.1 mol) thebaine in 0.4 liters dry benzene. After heating under reflux
for 2 hours, the reaction mixture is decomposed with a solution of 48 g
ammonium chloride in 200 ml water. The usual working up, after conversion
of the base into the hydrochloride by means of hydrogen chloride in ethyl
acetate, gives 7.3 g (21% of theory) (+/-)-2,12-dimethoxy-1-hydroxy-7-
methyl-6-phenethyl-5,6,8,9-tetrahydro-7H-dibenz[d,f]azonine hydrochloride,
melting point 227.6°C, after recrystallization from propan-2-ol.
