video tutorial Piperidine from the sodium metal reduction of pyridine

Name: video tutorial - Piperidine from the sodium metal reduction of pyridine
Uploaded: 2025-12-11T09:03:44.031Z
Duration: 14 min 58 s
Description: ring of the pyridine to form pi-pyridine. A pretty serious reduction. And it's going to...oil isn't as dry as we thought. 56 grams is a lot of sodium metal. Nearly two and a half moles.

Goal: reduce pyridine (15 g) to piperidine using a large excess of sodium metal in dry ethanol, yielding piperidine hydrochloride.
Reagents and quantities: 15 g pyridine; about 56 g sodium (≈2.5 mol; ~13 equiv per pyridine); absolute ethanol (~350 mL total); methanol added near the end; 20% HCl to form the hydrochloride salt.
Setup: 500 mL flask (larger recommended), vigorous stirring, and a large efficient reflux condenser to handle vigorous reaction and heat.
Procedure: add pyridine to ethanol, then introduce sodium chunks in stages; reaction runs vigorously with heating and formation of sodium ethoxide gel; after major sodium addition, add more ethanol to keep mixture liquid; near the end, add methanol to improve liquefaction; a trick discovered: methanol helps near the end.
Workup: hydrolyze sodium ethoxide with water to NaOH, then distill off ethanol and carefully add water to hydrolyze further, distilling piperidine with water; monitor pH and adjust with a small amount of acid to achieve slight acidity; distill again to remove solvents; a large-volume setup is helpful to avoid boil-overs; final distillate contains piperidine in ethanol/water (~500 mL collected).
Purification: convert piperidine to its hydrochloride salt by treating with HCl; isolate a crude crystallized product (~19 g), which indicates residual water/impurities; dissolve crude in ethanol to remove inorganic salts, filter, and evaporate to dryness to obtain a purer product.
Final result: 15.4 g of piperidine hydrochloride obtained after drying, representing about 95% yield relative to starting piperidine; color described as slightly off-white; purification attempt via solvent exchange (methanol/diethyl ether) suggested as a possible route for a white crystalline solid.
Notes: the process consumes large amounts of reagents and solvent; safety considerations (moisture control, boil-overs) emphasized; video mentions sponsorship and future reactions.