N-Phenethyl-4-piperidinone

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

N-Phenethyl-4-piperidinone
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
UNII
  • InChI=1S/C13H17NO/c15-13-7-10-14(11-8-13)9-6-12-4-2-1-3-5-12/h1-5H,6-11H2 Y
    Key: YDJXNYNKKXZBMP-UHFFFAOYSA-N Y
  • InChI=1/C13H17NO/c15-13-7-10-14(11-8-13)9-6-12-4-2-1-3-5-12/h1-5H,6-11H2
    Key: YDJXNYNKKXZBMP-UHFFFAOYAQ
  • O=C2CCN(CCc1ccccc1)CC2
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
GHS labelling:[1]
Warning
H302
P264, P270
NFPA 704 (fire diamond)
1
3
Legal status
  • AU: S9 (Prohibited substance)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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.

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.[2] 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.

References
  1. GHS: PubChem
  2. Schulz W. "Fentanyl". List of Top Pharmaceuticals. Chemical & Engineering News.

Further reading
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