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20-September-2008 09:55:56 - Piperidine 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 85.15 g/mol Appearance colourless liquid Density 0.862 g/ml, liquid Melting point -7 °C Boiling point 106 °C Solubility in water miscible Acidity pKa 11.24 Viscosity 1.573 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 references Piperidine is an organic compound with the molecular formula CH25NH. 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;1 the name comes from the genus name Piper, which is the Latin word for pepper.2 Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. Contents 1 Production 2 Natural occurrence of piperidine and derivatives 3 Conformation 4 Reactions 5 Uses 6 References Production Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum sulfide catalyst:3 C5H5N + 3 H2 → C5H10NH Pyridine can also be reduced to piperidine by sodium in ethanol.4 Natural occurrence of piperidine and derivatives Piperidine itself has been obtained from pepper5, from Psilocaulon absimile N.E.Br Aizoaceae6, and in Petrosimonia monandra.7 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 solenopsin8, the nicotine analog anabasine of the Tree Tobacco Nicotiana glauca, lobeline of the indian tobacco, the toxic alkaloids coniine and conhydrine from poison hemlock, which was used to put Socrates to death.9 Chemically similar to Piperidine is the chemical Piperazine which was named after Piperidine for its chemical similarity. Conformation Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N-H bond in an axial position, and the other in an equatorial position. After much controversy during the 1950s-1970s, the equatorial conformation was found to be more stable by 0.72 kcal/mol in the gas phase.10 In nonpolar solvents, a range between 0.2 and 0.6 kcal/mol has been estimated, but in polar solvents the axial conformer may be more stable.11 The two conformers interconvert rapidly through nitrogen inversion; the free energy activation barrier for this process, estimated at 6.1 kcal/mol, is substantially lower than the 10.4 kcal/mol for ring inversion.12 In the case of N-methylpiperidine, the equatorial conformation is preferred by 3.16 kcal/mol,10 which is much larger than the preference in methylcyclohexane, 1.74 kcal/mol. axial conformation equatorial conformation Reactions Piperidine is a widely used secondary amine. It is widely used to convert ketones to enamines.13 Enamines derived from piperidine can be used in the Stork enamine alkylation reaction.14 Piperidine can be converted to the chloramine C5H10NCl with calcium hypochlorite. The resulting chloramine undergoes dehydrohalogenation to afford the cyclic imine.15 Uses Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents. A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as a rubber vulcanization accelerator.3 Otherwise piperidine and its derivatives are common building blocks in the synthesis of pharmaceuticals and fine chemicals. A piperidine substructure can be found in many pharmaceuticals, including many antihistaminics, antipsychotics, and antidepressants. 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. 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.16 References ^ Frank Johnson Welcher 1947. Organic Analytical Reagents. D. Van Nostrand, 149. ^ Alexander Senning 2006. Elsevier's Dictionary of Chemoetymology. ISBN 0444522395. ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke Amines, Aliphatic Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH. doi:10.1002/14356007.a02_001 ^ C. S. Marvel and W. A. Lazier 1941. Benzoyl Piperidine. Org. Synth.; Coll. Vol. 1: 99. ^ Spaeth and Englaender, Ber.1935,68, 2218; cf. Pictet and Pictet, Helv. Chim. Acta, 1927, 10, 593 ^ Rimington, S. Afr. J. Sci, 1934, 31, 184 ^ Juraschewski and Stepanov, J. Gen. Chem., U.R.S.S., 1939, 9, 1687 ^ Arbiser JL, Kau T, Konar M et al. 2007. Solenopsin, the alkaloidal component of the fire ant Solenopsis invicta, is a naturally occurring inhibitor of phosphatidylinositol-3-kinase signaling and angiogenesis. Blood 109 2: 560-5. doi:10.1182/blood-2006-06-029934. PMID 16990598. ^ The Plant Alkaloids, Thomas Anderson Henry, 4th ed. 1949, The Blakiston Company ^ a b Luis Carballeira, Ignacio Pérez-Juste 1998. Influence of calculation level and effect of methylation on axial/equatorial equilibria in piperidines. Journal of Computational Chemistry 19 8: 961-976. doi:10.1002/SICI1096-987X19980619:8961::AID-JCC143.0.CO;2-A. ^ Ian D. Blackburne, Alan R. Katritzky, Yoshito Takeuchi 1975. Conformation of piperidine and of derivatives with additional ring hetero atoms. Acc. Chem. Res. 8 9: 300-306. doi:10.1021/ar50093a003. ^ F.A.L. Anet, Issa Yavari 1977. Nitrogen inversion in piperidine. J. Am. Chem. Soc. 99 8: 2794-2796. doi:10.1021/ja00450a064. ^ Vinayak V. Kane and Maitland Jones Jr 1990. Spiro5.7trideca-1,4-dien-3-one. Org. Synth.; Coll. Vol. 7: 473. ^ March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure Michael B. Smith, Jerry March Wiley-Interscience, 5th ion, 2001, ISBN 0-471-58589-0 ^ George P. Claxton, Lloyd Allen, and J. Martin Grisar 1988. 2,3,4,5-Tetrahydropyridine trimer. Org. Synth.; Coll. Vol. 6: 968. ^ List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control, International Narcotics Control Board Retrieved from http://en..org/wiki/Piperidine Categories: Piperidines | Amines | Amine solvents | DEA List I chemicals Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Nederlands 日本語 Polski Português Suomi Svenska 中文 This page was last modified on 19 August 2008, at 02:43
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