Potassium Iodide → alpha,alpha-Diphenyl-1-[3-(8-quinolinyloxy)propyl]-3-piperidinepropanenitrile hemihydrate

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Reaction Steps

A mixture of α,α-diphenyl-3-piperidinepropanenitrile (8.12 g, 0.028 mole), 8-(3-chloropropoxy)quinoline (6.18 g, 0.028 mole), and potassium carbonate (5.53 g, 0.04 mole) was heated at reflux overnight in 350 ml of 1-butanol containing potassium iodide (0.3 g). The reaction was filtered and stripped to dryness on a rotary evaporator. The residue obtained was dissolved in chloroform and extracted with 5% sodium hydroxide and water. The chloroform layer was dried over anhydrous sodium sulfate, filtered, and solvent removed to give a dark red mass. This material was subjected to flash chromatography on a silica gel column using 10% methanol-ethyl acetate, 20% methanol-ethyl acetate, and 50% methanol-ethyl acetate for elution. Fractions of similar purity were combined and solvent was removed by rotary evaporator. The red black residue obtained was dried in vacuo at 80° C. overnight. This furnished 5.29 g (39%) of a dark black residue. 1H NMR (CDCl3): σ 8.9 (m, 1, proton ortho to N in ring), 7.9-8.1 (m, l, proton para to N in ring), 6.9-7.6 (m, 14, aromatics), 4.2 (t, 2, methylenes adjacent to oxygen atom), 1.1-2.7 (m, 16, aliphatic portons and 1H from 0.5 H2O).

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