反应详情

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).

1. temperaturewas heated
2. temperatureThe solution was cooled
3. customthe solvent removed in vacuo
4. dissolutionThe residue was dissolved in methanol
5. additiontreated with sodium cyanoborohydride (1.25 g)
6. customThe solvent was then evaporated under reduced pressure
7. dissolutionthe residue dissolved in ethyl acetate
8. washwashed with water (2×50 ml), brine (1×50 ml)
9. dry with materialdried (magnesium sulphate)
10. filtrationfiltered
11. customevaporated
12. customThe residue was purified by column chromatography on silica