AskDefine | Define piperidine

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Noun

  1. An alicyclic heterocycle formally derived by the hydrogenation of pyridine; many of its derivatives are alkaloids or pharmaceuticals

Extensive Definition

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like, or similar to strong pungent cheese. Piperidine is a widely used building block in the synthesis of organic compounds, including pharmaceuticals.

Occurrence and production

The piperidine structural motif is present in numerous natural alkaloids such as quinine and piperine, the main active chemical agent in black pepper and relatives (Piper sp.), hence the name. Piperidine is also found in venom of fire ants and is the cause of the burning sensation associated with their bite.
Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum sulfide catalyst:
C5H5N + 2.5 H2 → C5H10NH
Pyridine can also be reduced to piperidine by sodium in ethanol.

Uses

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

Reagent in DNA sequencing

Piperidine is also commonly used in chemical degradation reactions, such as the sequencing of DNA in the cleavage of particular modified nucleotides. Piperidine is also commonly used as a base for the deprotection of Fmoc-amino acids used in solid-phase peptide synthesis.

Organic chemistry

Piperidine is a widely used secondary amine. It is widely used to convert ketones to enamines.
Piperidine can be converted to the chloramine C5H10NCl with calcium hypochlorite. The resulting chloramine undergoes dehydrohalogenation to afford the cyclic imine.

References

piperidine in German: Piperidin
piperidine in French: Pipéridine
piperidine in Dutch: Piperidine
piperidine in Japanese: ピペリジン
piperidine in Polish: Piperydyna
piperidine in Portuguese: Piperidina
piperidine in Finnish: Piperidiini
piperidine in Swedish: Piperidin
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