Reaktion #552624

Reaktionsgleichung

2-(3-chlorophenyl)-2-hydroxyethylamine carbonate

4-acetonylphenoxyacetonitrile

water

→

4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl] phenoxyacetonitrile

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   TemperaturThe solution was cooled
3. 3
   Sonstigethe solvent removed in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in methanol
5. 5
   workup.ADDITIONtreated with sodium cyanoborohydride (1.25 g)
6. 6
   SonstigeThe solvent was then evaporated under reduced pressure
7. 7
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
8. 8
   Waschenwashed with water (2×50 ml), brine (1×50 ml)
9. 9
   Trocknendried (magnesium sulphate)
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated
12. 12
    SonstigeThe residue was purified by column chromatography on silica

Vorschrift

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).

Quelle