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 ;
3D model (JSmol)	Interactive image;
Abbreviations	NPP
ChemSpider	87058 ;
ECHA InfoCard	100.049.630
PubChem CID	96437;
UNII	CIS0S4O95K ;
CompTox Dashboard (EPA)	DTXSID30192826 ;
	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 Key: YDJXNYNKKXZBMP-UHFFFAOYSA-N ; 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
EU classification (DSD) (outdated)	Flammable (F); Harmful (Xn); Dangerous for; the environment (N)
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

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.

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

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

External links

Beckett, A. H.; Casy, A. F.; Kirk, G. (1959). "Alpha- and Beta-Prodine Type Compounds". Journal of Medicinal Chemistry. 1 (1): 37–58. doi:10.1021/jm50002a004. PMID 13655028.

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[1] William Schulz. "Fentanyl". Chemical & Engineering News.