N-Phenethyl-4-piperidinone

N-Phenethyl-4-piperidone
IUPAC name 1-(2-Phenylethyl)piperidin-4-one
Other names N-Phenethyl-4-piperidone
Identifiers
CAS number	39742-60-4
PubChem	96437
ChemSpider	87058 Y
Jmol-3D images	Image 1
SMILES O=C2CCN(CCc1ccccc1)CC2
InChI 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
Properties
Molecular formula	C13H17NO
Molar mass	203.28 g mol−1
Melting point	56-60 °C, 269 K, -20 °F
Hazards
EU classification	Flammable (F) Harmful (Xn) Dangerous for the environment (N)
NFPA 704	3 1 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Phenethyl-4-piperidone (NPP) is a derivative of 4-piperidone with the molecular formula C₁₃H₁₇NO. 4-Piperidone 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

The synthesis of N-Phenethyl-4-piperidone cannot be prepared via the simple S_N2 substitution reaction reported on the web using 4-piperidone with phenethyl bromide in the presence of a phase transfer catalyst. It's preparation requires sophisticated laboratory equipment and considerable knowledge and skill with organic chemistry. It is made by the Claisen condensation of ethyl acrylate with 2 phenylethylamine.

http://commons.wikimedia.org/wiki/File:NPP.tif

Synthesis of NPP

Uses

N-Phenethyl-4-piperidone 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-piperidone 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

Beckett, A. H., A. F. Casey and G. Kirk, 1959, Alpha & beta prodine type compounds, J. Med. Chem, Vol 1, No.1