4-Piperidone

Last updated
4-Piperidone
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 (JSmol)
ChemSpider
ECHA InfoCard 100.050.420 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 255-481-1
PubChem CID
UNII
  • InChI=1S/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 Yes check.svgY
    Key: VRJHQPZVIGNGMX-UHFFFAOYSA-N Yes check.svgY
  • 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:
GHS-pictogram-exclam.svg
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)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
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).
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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 GuptaFent2.jpg
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

References

  1. ↑ Weintraub, Philip M.; Sabol, Jeffrey S.; Kane, John M.; Borcherding, David R. (2003). "Recent advances in the synthesis of piperidones and piperidines". Tetrahedron. 59 (17): 2953–2989. doi:10.1016/s0040-4020(03)00295-3.
  2. ↑ Gamrad, Waltraud; Dreier, Angelika; Goddard, Richard; Pörschke, Klaus-Richard (2015). "Cation-Cation Pairing by N-C-H⋅⋅⋅O Hydrogen Bonds". Angewandte Chemie International Edition. 54 (15): 4482–4487. doi:10.1002/anie.201408278. PMID   25712229.
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