Sodium Bicarbonate → HCID 19891053, compound

Participants

Reaction Steps

N-[3-(3-Aminophenoxy)propyl]-2,3-dihydro-5-methoxy-1,4-benzodioxin-2-methanamine dihydrochloride quarter hydrate (0.79 g, 1.9 mmole), prepared in Example 2 above, was dissolved in 26.5 ml of 48% HBr and refluxed under nitrogen for 23 hours. Upon cooling, the mixture was diluted to 250 ml with water and carefully neutralized with solid sodium bicarbonate. It was then extracted with two 200 ml portions of 3:1 dichloromethane/isopropanol and the combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to dryness in vacuum. The residue was column chromatographed on silica gel using 5% methanol/dichloromethane to which 1 ml/liter aqueous ammonia had been added. The product-containing fractions were combined, concentrated in vacuum, and the residue crystallized from 20 ml of isopropanol with the addition of 4 ml 4N HCl/isopropanol to give 0.33 g of the title compound (m.p. 183°-190° C.) as a beige solid, dihydrochloride.

Provenance & Evidence