Reaktion #49663

Reaktionsgleichung

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

4-chlorophenethyl bromide

potassium carbonate

→

title compound

1-(4-chlorophenethyl)-3-(R)-(+)-(1-cyano-1,1diphenylmethyl)piperidine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 4 hours
3. 3
   SonstigeThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml)
4. 4
   Sonstigethe layers separated
5. 5
   Extraktionthe aqueous layer extracted with dichloromethane (3×30 ml)
6. 6
   TrocknenThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto give an oil which
9. 9
   Sonstigewas purified by column chromatography on silica eluting with hexane
10. 10
    workup.ADDITIONcontaining dichloromethane (30% up to 70%)
11. 11
    workup.ADDITIONdichloromethane containing methanol (0% up to 5%)
12. 12
    Einengenconcentrated in vacuo
13. 13
    Sonstigeto give an oil which
14. 14
    Sonstigewas crystallised from acetonitrile

Vorschrift

A mixture containing 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)piperidine (1 g--see Preparation 1), 4-chlorophenethyl bromide (0.72 g), anhydrous potassium carbonate (1.5 g) and acetonitrile (25 ml) was heated under reflux for 4 hours. The mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml), the layers separated, and the aqueous layer extracted with dichloromethane (3×30 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing dichloromethane (30% up to 70%) and then dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from acetonitrile to give the title compound as colourless rhombs, yield 0.85 g, m.p. 129°14 131° C. [α]D25 +20.3 (c 1.0, CH2Cl2)

Quelle