Piperidine

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Piperidine (Azinane after the Hantzsch–Widman nomenclature) 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;[2] the name comes from the genus name Piper, which is the Latin word for pepper.[3] Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals.

Contents

Production

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst:[4]

Pyridine can also be reduced to piperidine by sodium in ethanol.[5]

Natural occurrence of piperidine and derivatives

Piperidine itself has been obtained from pepper[6], from Psilocaulon absimile N.E.Br (Aizoaceae)[7], and in Petrosimonia monandra.[8]

The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper the hot taste. This gave the compound its name. Other examples are the fire ant toxin solenopsin[9], the nicotine analog anabasine of the Tree Tobacco (Nicotiana glauca), lobeline of the indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.[10]

Conformation

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