4-Piperidone

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4-Piperidone
File:Piperidin-4-one-2D-skeletal.png
File:Piperidin-4-one-3D-balls.png
Names
Preferred IUPAC name
Piperidin-4-one
Other names
4-Piperidone
Azinanone
Azinan-4-one
Identifiers
3D model (JSmol)
ChemSpider
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EC Number
  • 255-481-1
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 checkY
    Key: VRJHQPZVIGNGMX-UHFFFAOYSA-N checkY
  • InChI=1/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2
    Key: VRJHQPZVIGNGMX-UHFFFAOYAC
  • O=C1CCNCC1
Properties
C5H9NO
Molar mass 99.133 g·mol−1
Boiling point 79 °C (174 °F; 352 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)

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1
3
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).

4-Piperidone is an organic compound with the molecular formula OC(CH2)4NH. It can be viewed as a derivative of piperidine. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Substituted and dehydro derivatives of 4-piperidinone are intermediates in alkaloid syntheses.[1]

The N-protonated derivative is typically isolated as the hydrate (HO)2C(CH2)4NH+2.[2]

It is a List I chemical in the United States as it is a precursor to fentanyl.

Fentanyl synthesis using the Gupta method starting from 4-piperidone
Fentanyl synthesis using the Gupta method starting from 4-piperidone

It is also used in the synthesis of NLX-204 and F-15,599.

See also

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References

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