Potassium Iodide → 3-(R)-(1-cyano-1,1-diphenylmethyl)-1-(4-hydroxy-3-methoxyphenethyl)piperidine

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A mixture containing 3-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine (0.3 g), 4-hydroxy-3-methoxyphenethyl chloride (0.233 g--see Preparation 6), anhydrous potassium carbonate (0.5 g), potassium iodide (0.2 g) and acetonitrile (15 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (40 ml) and 10% aqueous potassium 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 foam which was purified by column chromatography on silica eluting with dichloromethane containing methanol (5%). The product-containing fractions were combined and concentrated in vacuo to give a gum which was crystallised from acetonitrile to give the title compound as colourless rhombs, yield 0.132 g, m.p. 159-160°.

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