N-Phenethyl-4-piperidinone

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N-Phenethyl-4-piperidinone
Phenethylpiperidinone.png
Names
Preferred IUPAC name
1-(2-Phenylethyl)piperidin-4-one
Other names
1-Phenethylpiperidin-4-one (no longer recommended)
N-Phenylethyl-4-piperidinone
N-Phenethyl-4-piperidone
Identifiers
3D model (JSmol)
Abbreviations NPP
ChemSpider
ECHA InfoCard 100.049.630
Properties
C13H17NO
Molar mass 203.28 g/mol
Density 1.057 g/cm3
Melting point 56 to 60 °C (133 to 140 °F; 329 to 333 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., gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
Legal status
  • AU: S9 (Prohibited)
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

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[edit]

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[edit]

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.

NPPtofentanyl.gif

References[edit]

  1. ^ William Schulz. "Fentanyl". Chemical & Engineering News.

External links[edit]

  • Beckett, A. H.; Casy, A. F.; Kirk, G. (1959). "Alpha- and Beta-Prodine Type Compounds". Journal of Medicinal Chemistry. 1: 37–58. doi:10.1021/jm50002a004.