Piperidine
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| Names | |||
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Preferred IUPAC name
Piperidine
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| Other names
Hexahydropyridine
Azacyclohexane Pentamethyleneamine Azinane |
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| Identifiers | |||
110-89-4 
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| 3D model (Jmol) | Interactive image | ||
| ChEBI |
CHEBI:18049
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| ChEMBL |
ChEMBL15487
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| ChemSpider |
7791
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| ECHA InfoCard | 100.003.467 | ||
| 5477 | |||
| PubChem | 8082 | ||
| RTECS number | TM3500000 | ||
| UNII |
67I85E138Y
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| Properties | |||
| C5H11N | |||
| Molar mass | 85.15 g·mol−1 | ||
| Appearance | colourless liquid | ||
| Density | 0.862 g/mL, liquid | ||
| Melting point | −7 °C (19 °F; 266 K) | ||
| Boiling point | 106 °C (223 °F; 379 K) | ||
| miscible | |||
| Acidity (pKa) | 11.22 | ||
| -64.2·10−6 cm3/mol | |||
| Viscosity | 1.573 cP at 25 °C | ||
| Hazards | |||
| Safety data sheet | MSDS1,MSDS2 | ||
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EU classification (DSD)
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Flammable (F) Toxic (T) |
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| R-phrases | R11, R23/24, R34 | ||
| NFPA 704 | |||
| Related compounds | |||
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Related compounds
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pyridine pyrrolidine piperazine |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| Infobox references | |||
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.
Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson and again, independently, in 1852 by the French chemist Auguste Cahours, who named it. Both men obtained piperidine by reacting piperine with nitric acid.
Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst:
Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.
Piperidine itself has been obtained from black pepper, from Psilocaulon absimile (Aizoaceae), and in Petrosimonia monandra.
The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. This gave the compound its name. Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.
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