Piperidine

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (-CH2-) and one amine bridge (-NH-). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although, piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids.

Chemical Properties

Piperidine is a widely used secondary amine. It turns red litmus paper blue because it is basic. The conjugate acid has a pKa of 11.27 at 25 °C.

Synthesis

Piperidine can be prepared by hydrogenation of pyridine, usually over a cobalt or nickel catalyst.

Uses

Piperidine is used as a solvent and as a base. A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as a rubber vulcanization accelerator.

Safety

Piperidine is a strong base which can cause burns. Ingestion of piperidine may cause nausea, vomiting, and gastric disturbances. Breathing it in can cause respiratory tract irritation.

See Also

• Pyridine
• Amine
• Alkaloids
• Pharmaceuticals

References

Piperidine Resources
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