Hydrochloric Acid → 4-(4-Methoxybenzyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline

Participants

Reaction Steps

A mixture 28.4 g. (0.138 mole) of the hydrochloride salt of 2-aminoethyl)-1,2-dihydronaphthalene (II) in water (800 ml.) was acidified to pH 3 by the addition of hydrochloric acid. The resulting mixture was heated under reflux under a nitrogen atmosphere and with vigorous stirring, a solution of 38.0 g. (0.172 mole) of ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate in 200 ml. of ethanol was added dropwise over a period of 8 hours. Reflux was continued for 16 hours, then 300 ml. of concentrated hydrochloric acid was added. After a further 4 hours under reflux, the mixture was allowed to cool, and benzene (800 ml.), hexane (200 ml.) and methanol (200 ml.) were added, the mixture was shaken and the aqueous layer separated. The aqueous layer was basic and extracted with methylene chloride to give a 56 percent yield of product (III). The nuclear magnetic resonance spectrum of the product was consistent with the structure.

Provenance & Evidence