Phosphorus oxide (P4O10) → beta-[(5-Hydroxypentyl)amino]-4-methoxy-alpha-(4-methoxyphenyl)benzeneethanol fumarate hemihydrate

Participants

Reaction Conditions

Reaction Steps

A mixture of anisoin (10.0 g, 0.037 mole), 5-amino-1-pentanol (11.37 g, 0.11 mole) and phosphorus pentoxide (2.5 g, 0.018 mole) was heated for 4 hours in an oil bath at 105° C. with a nitrogen purge. Water was produced and evaporated as the reaction proceeded to completion. The reaction mixture was cooled and chloroform (100 ml) added. The chloroform layer was washed with dilute acid (100 ml×2). The aqueous washes were combined, made basic and washed with chloroform. The organic layer was concentrated and dissolved in 100 ml of ethanol, to which solution an aqueous solution of sodium borohydride (0.074 mole) was added. The resulting mixture was stirred for 1.5 hr and concentrated to dryness. The residue was partitioned between 100 ml of 25% sodium hydroxide and 500 ml of methylene chloride. The methylene chloride layer was washed with water (2×100 ml), concentrated and the concentrate was dissolved in methyl isobutylketone. Fumaric acid (0.037 mole) was added. The precipitate was recrystallized in acetone, filtered off and dried to give 7.09 g (52.9%) of crystals, m.p. 172°-175° C.

Provenance & Evidence