Nitric Acid → 4-(4-Nitrophenyl)piperidine

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Reaction Steps

4-Phenylpiperidine (22 g, 0.14 mol) was dissolved in concentrated sulphuric acid (44 g) and concentrated nitric acid (12 ml) was then added dropwise such that the temperature did not rise above 5° C. The reaction was then warmed slowly to room temperature and stirred overnight. The reaction mixture was then poured into water and made basic with 2N aqueous potassium hydroxide. After extraction with ether (3×150 ml), the combined organic extracts were dried with sodium sulphate and evaporated in vacuo. Recrystallisation from diethyl ether afforded the desired product as yellow crystals (11.4 g, 40% yield), M.pt. 90°-92° C.

Provenance & Evidence