Reaktion #49671

Reaktionsgleichung

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

4-carbamoylphenethyl bromide

potassium carbonate

→

title compound

3-(R, S)-(1-Cyano-1,1-diphenylmethyl)-1-(4-carbamoylphenethyl)piperidine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 5 hours
3. 3
   EinengenThe mixture was concentrated in vacuo
4. 4
   Sonstigethe residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml)
5. 5
   SonstigeThe layers were separated
6. 6
   Extraktionthe aqueous layer extracted with dichloromethane (3×20 ml)
7. 7
   TrocknenThe combined dichloromethane extracts were dried (MgSO4)
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto give a gum which
10. 10
    Sonstigewas purified by column chromatography on silica eluting with dichloromethane
11. 11
    workup.ADDITIONcontaining methanol (5%)
12. 12
    Einengenconcentrated inn vacuo

Vorschrift

A mixture containing 3-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidine (0.303 g), 4-carbamoylphenethyl bromide (0.275 g--see Preparation 5), anhydrous potassium carbonate (0.4 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (50 ml). The layers were separated and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated inn vacuo to give the title compound as a gum, yield 0.065 g.

Quelle