Water → 4-[2-[(3-Chloro-beta-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile

Participants

Reaction Steps

A mixture of 2-(3-chlorophenyl)-2-hydroxyethylamine carbonate (3.35 g) and 4-acetonylphenoxyacetonitrile in benzene was heated under reflux for 1 h with azeotropic removal of water using a Dean and Stark head. The solution was cooled, and the solvent removed in vacuo. The residue was dissolved in methanol and treated with sodium cyanoborohydride (1.25 g) and stirred for 5 h at ambient temperature. The solvent was then evaporated under reduced pressure, the residue dissolved in ethyl acetate, washed with water (2×50 ml), brine (1×50 ml), dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography on silica using methanol:chloroform 2:98 as eluent to give 4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile, (4.0 g).

Provenance & Evidence