N-Phenethyl-4-piperidinone

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N-Phenethyl-4-piperidinone
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Identifiers
CAS number 39742-60-4
PubChem 96437
ChemSpider 87058 7pxY
Jmol-3D images Image 1
Properties
Molecular formula C13H17NO
Molar mass Script error g mol−1
Density 1.057 g/cm3
Melting point 56 to 60 °C (133 to 140 °F; 329 to 333 K)
Hazards
EU classification Flammable (F)
Harmful (Xn)
Dangerous for
the environment (N)
NFPA 704

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

N-Phenethyl-4-piperidinone (NPP) is a derivative of 4-piperidinone with the molecular formula C13H17NO. 4-Piperidinone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs such as fentanyl.

Because of its possible use in the illicit manufacture of fentanyl, NPP was placed onto the list of controlled chemicals in the USA in 2007, and possession and sales of this compound are now restricted.

Preparation

N-Phenethyl-4-piperidinone can be prepared from 4-piperidinone and phenethyl bromide in biphasic conditions with a variety of phase transfer catalysts.[citation needed]

Uses

N-Phenethyl-4-piperidinone is useful in the synthesis of pharmaceuticals, primarily fentanyl and its analogs. Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 from NPP.[1] Janssen's synthesis involved reacting N-Phenethyl-4-piperidinone with aniline, and then reducing the imine product with sodium borohydride to 4-anilino-N-phenethylpiperidine (ANPP). This product is reacted with propionyl chloride to form fentanyl.

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References

External links

  • Beckett, A. H.; Casy, A. F.; Kirk, G. (1959). "Alpha- and Beta-Prodine Type Compounds". Journal of Medicinal Chemistry 1: 37. doi:10.1021/jm50002a004. 
      
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