Synthesis of Piperidine from Pyridine

Combine 200 mL of absolute ethanol and 15 g (14.7 mL) of pyridine in a reflux apparatus. Then start adding 56 g of dry sodium in large pieces, start vigorous stirring. When the solution becomes slurry add 20-50 mL of dry ethanol to dissolve the ethoxide you may need to do this many times, at the end add 30 mL of methanol. About 3 h later start to distill the solvents off, then add 200 mL of water in very small portions, otherwise, too much foam will be created. When all of the ethanol has been distilled off raise the temperature to distill off the aqueous piperidine. Then add about 25 mL of conc. HCl to the distillate to convert the piperidine to piperidine HCl. Then redistill to dryness with vacuum and recrystallize the crude piperidine HCl in hot ethanol.

Source

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After adding some sodium the ethanol started to reflux

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When the mixture forms slurry add some ethanol

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At the end of the reaction add some methanol

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Start to distill off the ethanol and add water in very small portions

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Crude piperidine water mixture, add the HCl to make piperidine HCl

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Distillation of the solution, dry and crude piperidine HCl is obtained

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