Piperidine
IUPAC name	Piperidine
Other names	Hexahydropyridine Azacyclohexane, pentamethyleneamine
Identifiers
CAS number	[110-89-4]
RTECS number	TM3500000
SMILES	C1CCCCN1
InChI	1/C5H11N/c1-2- 4-6-5-3-1/h6H,1-5H2
Properties
Molecular formula	C5H11N
Molar mass	85. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 15 g/mol
Appearance	colourless liquid
Density	0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 862 g/ml, liquid
Melting point	−7 °C
Boiling point	106 °C
Solubility in water	miscible
Acidity (pKa)	11. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 24
Viscosity	1. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 573 cP at 25 °C
Hazards
EU classification	Flammable (F) Toxic (T)
NFPA 704	3 3 3
R-phrases	R11, R23/24, R34
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) Infobox disclaimer and references

Piperidine is an organic compound with the molecular formula (CH₂)₅NH. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous Pyridine is a Chemical compound with the formula C5[[Hydrogen H5]] N. Pyrrolidine, also known as tetrahydropyrrole, is an Organic compound with the molecular formula C4H9N Piperazine is an Organic compound that consists of a six-membered ring containing two opposing nitrogen atoms In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. Methylene is the chemical species R2C named after Methane, in which two of the carbon atom's valence electrons form no bonds Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 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.

Contents 1 Occurrence and production 2 Uses 2.1 Use in pharmaceuticals 2.2 Illicit uses 2.3 Reagent in DNA sequencing 3 Organic chemistry 4 See also 5 References

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. This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. Quinine (ˈkwaɪnaɪn kwɪˈniːn ˈkwiːniːn is a natural white Crystalline Alkaloid having Antipyretic (fever-reducing antimalarial, Piperine is the Alkaloid responsible for the Pungency of Black pepper and Long pepper, along with Chavicine (an Isomer Black pepper ( Piper nigrum) is a flowering Vine in the family Piperaceae, cultivated for its Fruit, which is usually dried Piper, the pepper plants or pepper vines (a term used for certain Clematis in older times are an economically and ecologically ), hence the name. Piperidine is also found in venom of fire ants and is the cause of the burning sensation associated with their bite. Fire ants, (referred to as red ants in the UK) are stinging Ants with over 280 species worldwide

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum sulfide catalyst:^[1]

C₅H₅N + 2. 5 H₂ → C₅H₁₀NH

Pyridine can also be reduced to piperidine by sodium in ethanol. ^[2]

Uses

A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as a rubber vulcanization accelerator. Vulcanization (or Vulcanisation refers to a specific curing process of Rubber involving high heat and the addition of Sulfur or other equivalent curatives ^[1]

Use in pharmaceuticals

Otherwise piperidine and its derivatives are widely used building blocks in the synthesis of pharmaceuticals. Piperidine is found in the following drugs: raloxifene, minoxidil, thioridazine, haloperidol, droperidol, and mesoridazine. Raloxifene is an oral Selective estrogen receptor modulator (SERM that has estrogenic actions on bone and anti-estrogenic actions on the uterus and breast Minoxidil (trade names Rogaine and Regaine) is a Vasodilator Medication known for its ability to slow or stop hair loss and promote Thioridazine is a Piperidine Antipsychotic drug belonging to the Phenothiazine drug group and was previously widely used in the treatment Haloperidol is a Typical antipsychotic. It is in the Butyrophenone class of Antipsychotic medications and has pharmacological effects similar Droperidol ( Dropletan, Dridol or Inapsine) is an Antidopaminergic drug used as an Antiemetic and antipsychotic Mesoridazine (sold as Serentil) is a Piperidine Neuroleptic drug belonging to the class of drugs called Phenothiazines used in the treatment Many pharmaceutical drugs contain a piperidine ring because the group tends to impart favorable pharmacokinetic properties such as water solubility and bioavailability. Pharmacokinetics (in Greek: “pharmacon” meaning drug and “kinetikos” meaning putting in motion the study of time dependency sometimes abbreviated as “PK” is a In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Most piperidines induce the liver enzyme CYP2D6, resulting in faster metabolism, such as in many beta-blockers and antiarrhythmics. Cytochrome P450 2D6 (CYP2D6 a member of the Cytochrome P450 mixed-function oxidase system is one of the most important enzymes involved in the metabolism of Xenobiotics Beta blockers (sometimes written as β-blocker) are a class of drugs used for various indications but particularly for the management of Cardiac arrhythmias Antiarrhythmic agents are a group of Pharmaceuticals that are used to suppress fast rhythms of the Heart ( Cardiac arrhythmias) such as Atrial fibrillation

Illicit uses

Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances due to its use (peaking in the 1970s) in the clandestine manufacture of PCP (also known as angel dust). The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances is one of three major drug control treaties currently in force This article is about the Decade 1970-1979 For the Year 1970 see 1970. Phencyclidine (a complex clip of the chemical name phenylcyclohexylpiperidine, commonly initialised as PCP) is a Dissociative drug ^[3]

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. In Organic chemistry, peptide synthesis is the production of Peptides which are Organic compounds in which multiple Amino acids are linked via In Organic chemistry, peptide synthesis is the production of Peptides which are Organic compounds in which multiple Amino acids are linked via

Organic chemistry

Piperidine is a widely used secondary amine. It is widely used to convert ketones to enamines. A ketone (pronounced as key tone) is either the Functional group characterized by a Carbonyl group (O=C linked to two other Carbon atoms or An enamine is an unsaturated compound derived by the reaction of an Aldehyde or Ketone with a Secondary amine followed by loss of H2O ^[4]

Piperidine can be converted to the chloramine C₅H₁₀NCl with calcium hypochlorite. Calcium hypochlorite is a Chemical compound with formula (2 It is widely used for Water treatment and as a Bleaching agent (bleaching The resulting chloramine undergoes dehydrohalogenation to afford the cyclic imine. Dehydrohalogenation is an Organic chemistry reaction from which an Alkene is obtained from an Alkyl halide. ^[5]

See also

• Piperazine
• Pyridine

References

1. ^ ^{a b} Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke “Amines, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH. Piperazine is an Organic compound that consists of a six-membered ring containing two opposing nitrogen atoms Pyridine is a Chemical compound with the formula C5[[Hydrogen H5]] N. doi:10.1002/14356007.a02_001
2. ^ C. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. S. Marvel and W. A. Lazier (1941). "Benzoyl Piperidine". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 1: 99.  
3. ^ List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control, International Narcotics Control Board
4. ^ Vinayak V. Kane and Maitland Jones Jr (1990). "Spiro[5.7trideca-1,4-dien-3-one]". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 7: 473.  
5. ^ George P. Claxton, Lloyd Allen, and J. Martin Grisar (1988). "2,3,4,5-Tetrahydropyridine trimer". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 6: 968.  

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