PIPERIDINE

Piperidine
Piperidine Piperidine
General
Systematic name	Piperidine
Other names	Hexahydropyridine Azacyclohexane, pentamethyleneamine
Molecular formula	C5H11N
SMILES	C1CCCCN1
Molar mass	85.15 g/mol
Appearance	colourless liquid
CAS number	[110-89-4]
Properties
Density and phase	0.862 g/ml, liquid
Solubility in water	miscible
Melting point	−7 °C
Boiling point	106 °C
Acidity (p''K''a)	11.24
Basicity (p''K''b)	2.87
Viscosity	? cP at ? °C
Hazards
MSDS	External MSDS
EU classification	Flammable ('F') Toxic ('T')
NFPA 704
R-phrases	, ,
S-phrases	, , , ,
Flash point	16 °C
RTECS number	TM3500000
Related compounds
Related compounds	pyridine pyrrolidine piperazine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

'Piperidine' is an organic compound with the molecular formula C₅H₁₁N. It is a heterocyclic amine with a six-membered ring containing five carbon atoms and one nitrogen atom. It is a clear liquid with a pepper-like odor.
The piperidine structural motif is present in numerous natural alkaloids such as piperine and quinine, and is the main active chemical agent in black pepper and relatives (''Piper sp.''), hence the name. Piperidine is also a structural element of many pharmaceutical drugs such as raloxifene, minoxidil, thioridazine and mesoridazine.
Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1] due to its use (peaking in the 1970s) in the clandestine manufacture of PCP. It is also a byproduct of burning phencyclidine (PCP, phenylcyclohexylpiperidine).
Piperidine is often used as a solvent for its mild basic properties, most notably in Fmoc-strategy solid phase peptide synthesis.
The major industrial application of piperidine is for the production of dipiperidinyl dithium tetrasulfide, which is used as a rubber vulcanization accelerator.
Piperidine is naturally found in fire ant venom, and is the cause of the burning sensation associated with the bite of these insects.
Piperidine is also commonly used in chemical degradation reactions, such as the DNA sequencing method invented by Walter Gilbert in 1977, for cleavage of particular modified nucleotides. Piperidine is also commonly used as a strong base for the deprotection of amino acids in solid-phase peptide synthesis.

Contents

Use in pharmaceutical drugs

See also

External links

Use in pharmaceutical drugs

Many pharmaceutical drugs contain a piperidine ring because the group tends to impart drug-like physical properties such as water solubility and bioavailability. Examples of drugs that contain piperidines include mesoridazine, thioridazine, haloperidol, droperidol, benperidol, and risperidone.

See also

★ Piperazine

External links

★ International Chemical Safety Card 0317