Potassium Carbonate → 3-(R)-(1-cyano-1,1-diphenylmethyl)-1-[2-(indan-5-yl)ethyl]piperidine

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Reaction Steps

A mixture containing 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)piperidine (0.28 g), 5-(2-bromoethyl)indane (0.23 g--see Preparation 4), anhydrous potassium carbonate (0.3 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (20 ml), the layers 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 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 rhombs, yield 0.13 g, m.p. 88°-91° C.

Provenance & Evidence