反应详情

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)

1. temperaturewas heated
2. temperatureunder reflux for 4 hours
3. customThe mixture was partitioned between dichloromethane (50 ml) and 10% aqueous potassium carbonate (30 ml)
4. customthe layers separated
5. extractionthe aqueous layer extracted with dichloromethane (3×30 ml)
6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto give an oil which
9. customwas purified by column chromatography on silica eluting with hexane
10. additioncontaining dichloromethane (30% up to 70%)
11. additiondichloromethane containing methanol (0% up to 5%)
12. concentrationconcentrated in vacuo
13. customto give an oil which
14. customwas crystallised from acetonitrile