4-Phenyl-1,3-benzodioxans

#1. Field of the Invention

#This invention relates to novel optionally substituted 2-aminomethyl-4-phenyl-1,3-benzodioxans and derivatives thereof which possess valuable anticonvulsant and antiarrhythmia activity.

#2. Description of the Prior Art

#5-Chloro-2-hydroxybenzophenone (100.0 g, 0.429 mole) was dissolved with stirring, under anhydrous conditions, in 1 liter of anhydrous THF (tetrahydrofuran) contained in a 5 1. flask. The flask was immersed in an ice-water bath, the solution was stirred vigorously, and 450 ml (0.45 mole) of diborane in THF soln (1M as BH.sub.3) was immediately added from a dropping funnel as rapidly as maintaining control of the reaction would allow; about 4 minutes was required. Foaming occurred and the color of the reaction mixture deepened, then lightened. After addition, the colorless solution was stirred in the cooling bath for 15 minutes and was then poured slowly, cautiously, and with good stirring onto a mixture of cracked ice and 700 ml of 5% HC1 soln.

#The insoluble material was extracted out with 3 portions of ether; the combined extracts were washed with dilute NaHCO.sub.3 soln (2 portions), water (1 portion) and saturated brine (1 portion) and dried over anhydrous MgSO.sub.4. Evaporation of the solvents gave an oil which was taken up in hot cyclohexane; the solvent was evaporated and the residue was stripped in vacuum. The oil thus obtained was dissolved i 1200 ml of hot cyclohexane; the solution was filtered, seeded, and allowed to stand at room temperature.

#The solid was filtered, washed with cyclohexane, and air-dried. Light cream-colored crystals, mp 93.degree.-95.degree., were obtained. The yield was 64.5 g (62%).