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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&section=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&section=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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