Reaktion #49677

Reaktionsgleichung

3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine

4-hydroxyphenethyl bromide

sodium bicarbonate

→

title compound

3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)-1-(4-hydroxyphenethyl)piperidine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 5 hours
3. 3
   SonstigeThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
4. 4
   Sonstigethe layers separated
5. 5
   Extraktionthe aqueous layer extracted with dichloromethane (2×50 ml)
6. 6
   TrocknenThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto give a gum which
9. 9
   Sonstigewas purified by column chromatography, firstly on silica eluting with dichlorometbane
10. 10
    workup.ADDITIONcontaining methanol (0% up to 6%)
11. 11
    workup.ADDITIONon alumina eluting with dichloromethane containing methanol (0% up to 10%)
12. 12
    Einengenconcentrated in vacuo

Vorschrift

A mixture containing 3-(R,S)-(1-carbamoyl-1,1-diphenylmethyl)piperidine (0.3 g), 4-hydroxyphenethyl bromide (0.21 g), sodium bicarbonate (0.3 g) and acetonitrile (15 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography, firstly on silica eluting with dichlorometbane containing methanol (0% up to 6%), and then on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as colourless microcrystals, yield 0.042 g, m.p. 135°-140° C.

Quelle