Water → 2,3-dihydro-6-methoxy-2-methyl-N-propyl-4-benzofuranamine

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Reaction Steps

A solution of 3.2 grams of N-(2,3-dihydro-6-methoxy-2-methyl-4-benzofuranyl)propanamide, prepared in the foregoing example, in 30 cc of anhydrous benzene is gradually added into a suspension of 1.1 grams of LiAlH4 in 30 cc of anhydrous ethyl ether at 0° C. and the resulting reaction mixture is heated to the reflux temperature for 6 hours. At the end of this time the temperature is decreased to 0° C. and the aluminum complex is decomposed by addition of 3.3 cc of water. After 30 minutes of stirring at room temperature, the inorganic salts are discarded by filtration and the filtrate, dried over Na2SO4, is concentrated to dryness. The under vacuum distillation of the obtained residue affords 2.8 grams (93 percent of theoretical) of the title compound. B.p./0.2 mmHg 140°-142° C. The corresponding hydrochloride prepared by treatment of the free base with HCl melts at 110°-111° C.

Provenance & Evidence