Piper i Dine
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7/28/2019 Piper i Dine
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Piperidine (Azinane after the HantzschWidman nomenclature) is anorganic compound with the
molecular formula (CH2)5NH. This heterocyclicamine consists of a six-membered ring containing
fivemethyleneunits and one nitrogenatom. It is a colorless fuming liquid with an odor described as
ammoniacal, pepper-like;[2] the name comes from the genus namePiper, which is the Latin word for
pepper.[3] Piperidine is a widely used building block and chemical reagentin the synthesis of organic
compounds, including pharmaceuticals.
Production
Industrially, piperidine is produced by the hydrogenationofpyridine, usually over a molybdenum
disulfide catalyst:[4]
C5H5N + 3 H2 C5H10NH
Pyridine can also be reduced to piperidine bysodium in ethanol.[5]
[edit]Natural occurrence of piperidine and derivatives
Piperidine itself has been obtained fromblack 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 includepiperine,
which gives black pepperits spicy taste. This gave the compound its name. Other examples are
the fire anttoxin solenopsin,[9]the nicotine analog anabasine of the Tree Tobacco (Nicotiana
glauca),lobeline of theindian tobacco, and the toxic alkaloid coniinefrom poison hemlock, which
was used to put Socratesto death.[10]
Uses
Piperidine is used as asolvent and as a base. The same is true for certain derivatives: N-
formylpiperidine is a polar aprotic solventwith better hydrocarbon solubility than other amide solvents,
and2,2,6,6-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 ofdipiperidinyl dithiuram
tetrasulfide, which is used as a rubbervulcanization accelerator. [4]
Otherwise piperidine and its derivatives are ubiquitous building blocks in the synthesis of
pharmaceuticals and fine chemicals. The piperidine structure is e.g. found in the
pharmaceuticalsparoxetine,risperidone,methylphenidate,raloxifene,minoxidil,thioridazine,haloperi
dol,droperidol, mesoridazine, meperidine, melperone the psychochemical agents Ditran-B (JB-
329),N-methyl-3-piperidyl benzilate (JB-336) and in many others.
http://en.wikipedia.org/wiki/Hantzsch%E2%80%93Widman_nomenclaturehttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Methyleneshttp://en.wikipedia.org/wiki/Methyleneshttp://en.wikipedia.org/wiki/Methyleneshttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Piperidine#cite_note-1http://en.wikipedia.org/wiki/Piper_(genus)http://en.wikipedia.org/wiki/Piper_(genus)http://en.wikipedia.org/wiki/Piperidine#cite_note-2http://en.wikipedia.org/wiki/Chemical_reagenthttp://en.wikipedia.org/wiki/Chemical_reagenthttp://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Molybdenum_disulfidehttp://en.wikipedia.org/wiki/Molybdenum_disulfidehttp://en.wikipedia.org/wiki/Piperidine#cite_note-Ullmann-3http://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Ethanolhttp://en.wikipedia.org/wiki/Piperidine#cite_note-4http://en.wikipedia.org/w/index.php?title=Piperidine&action=edit§ion=2http://en.wikipedia.org/wiki/Black_pepperhttp://en.wikipedia.org/wiki/Black_pepperhttp://en.wikipedia.org/wiki/Piperidine#cite_note-5http://en.wikipedia.org/wiki/Piperidine#cite_note-6http://en.wikipedia.org/wiki/Piperidine#cite_note-7http://en.wikipedia.org/wiki/Piperidine#cite_note-7http://en.wikipedia.org/wiki/Alkaloidhttp://en.wikipedia.org/wiki/Piperinehttp://en.wikipedia.org/wiki/Piperinehttp://en.wikipedia.org/wiki/Black_pepperhttp://en.wikipedia.org/wiki/Fire_anthttp://en.wikipedia.org/wiki/Fire_anthttp://en.wikipedia.org/wiki/Solenopsinhttp://en.wikipedia.org/wiki/Piperidine#cite_note-bowen-8http://en.wikipedia.org/wiki/Piperidine#cite_note-bowen-8http://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Anabasinehttp://en.wikipedia.org/wiki/Nicotiana_glaucahttp://en.wikipedia.org/wiki/Nicotiana_glaucahttp://en.wikipedia.org/wiki/Lobelinehttp://en.wikipedia.org/wiki/Lobelinehttp://en.wikipedia.org/wiki/Indian_tobaccohttp://en.wikipedia.org/wiki/Indian_tobaccohttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Poison_hemlockhttp://en.wikipedia.org/wiki/Poison_hemlockhttp://en.wikipedia.org/wiki/Socrateshttp://en.wikipedia.org/wiki/Socrateshttp://en.wikipedia.org/wiki/Piperidine#cite_note-9http://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/N-formylpiperidinehttp://en.wikipedia.org/wiki/N-formylpiperidinehttp://en.wikipedia.org/wiki/N-formylpiperidinehttp://en.wikipedia.org/wiki/Polar_aprotic_solventhttp://en.wikipedia.org/wiki/Polar_aprotic_solventhttp://en.wikipedia.org/wiki/2,2,6,6-tetramethylpiperidinehttp://en.wikipedia.org/wiki/2,2,6,6-tetramethylpiperidinehttp://en.wikipedia.org/wiki/2,2,6,6-tetramethylpiperidinehttp://en.wikipedia.org/wiki/Steric_effectshttp://en.wikipedia.org/wiki/Nucleophilicityhttp://en.wikipedia.org/wiki/Organic_solventhttp://en.wikipedia.org/w/index.php?title=Dipiperidinyl_dithiuram_tetrasulfide&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Dipiperidinyl_dithiuram_tetrasulfide&action=edit&redlink=1http://en.wikipedia.org/wiki/Vulcanizationhttp://en.wikipedia.org/wiki/Piperidine#cite_note-Ullmann-3http://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/Risperidonehttp://en.wikipedia.org/wiki/Risperidonehttp://en.wikipedia.org/wiki/Methylphenidatehttp://en.wikipedia.org/wiki/Methylphenidatehttp://en.wikipedia.org/wiki/Raloxifenehttp://en.wikipedia.org/wiki/Raloxifenehttp://en.wikipedia.org/wiki/Minoxidilhttp://en.wikipedia.org/wiki/Thioridazinehttp://en.wikipedia.org/wiki/Thioridazinehttp://en.wikipedia.org/wiki/Thioridazinehttp://en.wikipedia.org/wiki/Haloperidolhttp://en.wikipedia.org/wiki/Haloperidolhttp://en.wikipedia.org/wiki/Haloperidolhttp://en.wikipedia.org/wiki/Droperidolhttp://en.wikipedia.org/wiki/Mesoridazinehttp://en.wikipedia.org/wiki/Meperidinehttp://en.wikipedia.org/wiki/Melperonehttp://en.wikipedia.org/wiki/Ditranhttp://en.wikipedia.org/wiki/N-methyl-3-piperidyl_benzilatehttp://en.wikipedia.org/wiki/N-methyl-3-piperidyl_benzilatehttp://en.wikipedia.org/wiki/Hantzsch%E2%80%93Widman_nomenclaturehttp://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Aminehttp://en.wikipedia.org/wiki/Methyleneshttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Piperidine#cite_note-1http://en.wikipedia.org/wiki/Piper_(genus)http://en.wikipedia.org/wiki/Piperidine#cite_note-2http://en.wikipedia.org/wiki/Chemical_reagenthttp://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Molybdenum_disulfidehttp://en.wikipedia.org/wiki/Molybdenum_disulfidehttp://en.wikipedia.org/wiki/Piperidine#cite_note-Ullmann-3http://en.wikipedia.org/wiki/Sodiumhttp://en.wikipedia.org/wiki/Ethanolhttp://en.wikipedia.org/wiki/Piperidine#cite_note-4http://en.wikipedia.org/w/index.php?title=Piperidine&action=edit§ion=2http://en.wikipedia.org/wiki/Black_pepperhttp://en.wikipedia.org/wiki/Piperidine#cite_note-5http://en.wikipedia.org/wiki/Piperidine#cite_note-6http://en.wikipedia.org/wiki/Piperidine#cite_note-7http://en.wikipedia.org/wiki/Alkaloidhttp://en.wikipedia.org/wiki/Piperinehttp://en.wikipedia.org/wiki/Black_pepperhttp://en.wikipedia.org/wiki/Fire_anthttp://en.wikipedia.org/wiki/Solenopsinhttp://en.wikipedia.org/wiki/Piperidine#cite_note-bowen-8http://en.wikipedia.org/wiki/Nicotinehttp://en.wikipedia.org/wiki/Anabasinehttp://en.wikipedia.org/wiki/Nicotiana_glaucahttp://en.wikipedia.org/wiki/Nicotiana_glaucahttp://en.wikipedia.org/wiki/Lobelinehttp://en.wikipedia.org/wiki/Indian_tobaccohttp://en.wikipedia.org/wiki/Coniinehttp://en.wikipedia.org/wiki/Poison_hemlockhttp://en.wikipedia.org/wiki/Socrateshttp://en.wikipedia.org/wiki/Piperidine#cite_note-9http://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Base_(chemistry)http://en.wikipedia.org/wiki/N-formylpiperidinehttp://en.wikipedia.org/wiki/N-formylpiperidinehttp://en.wikipedia.org/wiki/Polar_aprotic_solventhttp://en.wikipedia.org/wiki/2,2,6,6-tetramethylpiperidinehttp://en.wikipedia.org/wiki/Steric_effectshttp://en.wikipedia.org/wiki/Nucleophilicityhttp://en.wikipedia.org/wiki/Organic_solventhttp://en.wikipedia.org/w/index.php?title=Dipiperidinyl_dithiuram_tetrasulfide&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Dipiperidinyl_dithiuram_tetrasulfide&action=edit&redlink=1http://en.wikipedia.org/wiki/Vulcanizationhttp://en.wikipedia.org/wiki/Piperidine#cite_note-Ullmann-3http://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/Risperidonehttp://en.wikipedia.org/wiki/Methylphenidatehttp://en.wikipedia.org/wiki/Raloxifenehttp://en.wikipedia.org/wiki/Minoxidilhttp://en.wikipedia.org/wiki/Thioridazinehttp://en.wikipedia.org/wiki/Haloperidolhttp://en.wikipedia.org/wiki/Haloperidolhttp://en.wikipedia.org/wiki/Droperidolhttp://en.wikipedia.org/wiki/Mesoridazinehttp://en.wikipedia.org/wiki/Meperidinehttp://en.wikipedia.org/wiki/Melperonehttp://en.wikipedia.org/wiki/Ditranhttp://en.wikipedia.org/wiki/N-methyl-3-piperidyl_benzilate 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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 ofFmoc-amino acids used in solid-phasepeptide 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 clandestinemanufacture ofPCP (also known as angel dust, sherms, wet, etc.).[
http://en.wikipedia.org/wiki/Fmochttp://en.wikipedia.org/wiki/Peptide_synthesishttp://en.wikipedia.org/wiki/Peptide_synthesishttp://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Phenylcyclohexylpiperidinehttp://en.wikipedia.org/wiki/Phenylcyclohexylpiperidinehttp://en.wikipedia.org/wiki/Piperidine#cite_note-16http://en.wikipedia.org/wiki/Fmochttp://en.wikipedia.org/wiki/Peptide_synthesishttp://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Phenylcyclohexylpiperidinehttp://en.wikipedia.org/wiki/Piperidine#cite_note-16 -
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