Réaction #49672

Équation de réaction

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

3,4-methylenedioxybenzyl chloride

potassium carbonate

→

title compound

3-(R, S)-(1-cyano-1,1-diphenylmethyl)-1-(3,4-methylenedioxybenzyl)piperidine

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 16 hours
3. 3
   AutreThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
4. 4
   Autrethe layers separated
5. 5
   Extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
6. 6
   SéchageThe combined dichloromethane extracts were dried (MgSO4)
7. 7
   Concentrationconcentrated in vacuo
8. 8
   Autreto give a gum which
9. 9
   Autrewas purified by column chromatography on silica eluting with dichloromethane
10. 10
    workup.ADDITIONcontaining methanol (0% up to 2%)
11. 11
    Concentrationconcentrated in vacuo

Mode opératoire

A mixture containing 3-(R,S)-(1-cyano-1,1-diphenylmethyl)piperidine (0.27 g), 3,4-methylenedioxybenzyl chloride (0.18 g), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 16 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 (2×30 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 (0% up to 2%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless solid, yield 0.2 g, m.p. 127°-130° C.

Source