Reacción #49667

Ecuación de reacción

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

4-methylphenethyl bromide

potassium carbonate

→

title compound

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

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 5 hours
3. 3
   OtroThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml)
4. 4
   Otrothe layers separated
5. 5
   Extracciónthe aqueous layer extracted with dichloromethane (3×30 ml)
6. 6
   SecadoThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto give an oil which
9. 9
   Otrowas 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
    Concentraciónconcentrated in vacuo
13. 13
    Otroto give an oil which
14. 14
    Otrowas crystallised from acetonitrile

Procedimiento

A mixture containing 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)piperidine (1 g), 4-methylphenethyl bromide (0.72 g) , anhydrous potassium carbonate (1.5 g) and acetonitrile (25 ml) was heated under reflux for 5 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%) 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 rbombs, yield 1 g, m.p. 110°-113° C. [α]D25 +14.7 (c 1.0 CH2Cl2).

Fuente