2-(2-Chlorophenoxymethyl)oxirane → N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride

Participants

Reaction Steps

A mixture of 2-amino-7-hydroxytetralin (1.9 g) and 1-(2-chlorophenoxy)-2,3-epoxypropane (2.15 g) in absolute ethanol (60 ml) is refluxed for 5 hours and then ethanol is evaporated off under reduced pressure. The thus obtained residue is chromatographed on a silica gel column eluting first with ethyl acetate up to the complete elution of the first spot and then with a mixture ethyl acetate/methanol 9/1 v/v. The obtained fractions are pooled and concentrated to dryness. The residue is dissolved in isopropanol (20 ml) and the obtained solution is acidified by the addition of HC1/isopropanol. The precipitate is recovered by filtration yielding 2.25 g of N-(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-chlorophenoxy)propanamine hydrochloride; m.p. 201°-203° C.

Provenance & Evidence