4-Piperidinone

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4-Piperidinone
Piperidin-4-one-2D-skeletal.png
Piperidin-4-one-3D-balls.png
Names
Preferred IUPAC name
Piperidin-4-one
Other names
4-Piperidone
Azinanone
Azinan-4-one
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.050.420
Properties
C5H9NO
Molar mass 99.13 g·mol−1
Boiling point 79 °C (174 °F; 352 K)
Hazards
Flammable (F)
Harmful (Xn)
Dangerous for
the environment (N)
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 91 °C (196 °F; 364 K)
Related compounds
Related compounds
Piperidine; 2-Piperidinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Piperidinone is a derivative of piperidine with the molecular formula C5H9NO. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs.

Piperidones[edit]

Piperidones are a class of chemical compounds sharing the piperidone skeleton. A classic named reaction for the synthesis of piperidones is the Petrenko-Kritschenko piperidone synthesis which involves combining an alkyl-1,3-acetonedicarboxylate with benzaldehyde and an amine.[1] This multicomponent reaction is related to the Hantzsch pyridine synthesis.

1-Methyl-4-piperidone is a starting material in the synthesis of dorastine, propiverine and piperylone. 1,3-dimethyl-4-piperidone is used to make naranol. 1-Benzyl-4-piperidone is a starting material for fentanyl,[2] carpipramine, clocapramine, Fluspirilene, pipamperone, Benzetimide, Aplaviroc and Osanetant. N-Carboethoxy-4-piperidone was used to make Lorcainide.

N-Benzyl-4-piperidone is made when 1 equivalent of benzylamine is condensed with 2 molecules of ethylacrylate and the double conjugate addition product is subject of a Dieckmann cyclization followed by saponification and decarboxylation. Note that the intermediate 3-carboethoxy-N-Benzyl-4-piperidone prior to saponification can be used as a product to make Pimozide, Benperidol and droperidol.

See also[edit]

References[edit]

  1. ^ Ueber die Condensation von Aceton-dicarbonsäureestern mit Benzaldehyd unter Anwendung von Ammoniak P. Petrenko-Kritschenko, N. Zoneff Berichte der deutschen chemischen Gesellschaft Volume 39 Issue 2, Pages 1358 - 1361 1906 doi:10.1002/cber.19060390234
  2. ^ Janssen, Paul A. J. (1965). "1-aralkyl-4-(n-aryl-carbonyl amino)-piperidines and related compounds US3,164,600A" (PDF). Google Patents. Vosselaar, Belgium: Research Laboratorium Dr. C. Janssen. Retrieved 26 December 2016.