Chemistry:N-Phenethyl-4-piperidinone

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
CAS Number	39742-60-4 Y
3D model (JSmol)	Interactive image
Abbreviations	NPP
ChemSpider	87058 Y
PubChem CID	96437
UNII	CIS0S4O95K Y
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
SMILES O=C2CCN(CCc1ccccc1)CC2
Properties
Chemical formula	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 pictograms
GHS Signal word	warning
NFPA 704 (fire diamond)	3 1
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).
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Infobox references

Tracking categories (test):

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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.

Because of its possible use in the illicit manufacture of fentanyl, the United States Drug Enforcement Administration (DEA) placed NPP under control as a List 1 Chemical in 2007. Both domestic sales and domestic importations are thus subject to DEA reporting requirements.

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 Benzylfentanyl. The Siegfried method (shown below and published on The Hive) involves 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.

Further reading

• "Alpha- and beta-prodine type compounds". Journal of Medicinal and Pharmaceutical Chemistry 1 (1): 37–58. February 1959. doi:10.1021/jm50002a004. PMID 13655028.