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 checkY
3D model (JSmol)
  • Interactive image
Abbreviations NPP
ChemSpider
  • 87058 checkY
ECHA InfoCard 100.049.630 Edit this at Wikidata
PubChem CID
  • 96437
UNII
  • CIS0S4O95K checkY
CompTox Dashboard (EPA)
  • DTXSID30192826 Edit this at Wikidata
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 checkY
    Key: YDJXNYNKKXZBMP-UHFFFAOYSA-N checkY
  • 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
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 labelling:[1]
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H302
Precautionary statements
 P264, P270
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability (yellow): no hazard codeSpecial hazards (white): no code
1
3
Legal status
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
Chemical compound

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.[3]

Preparation

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

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.[4] 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.

References

  1. ^ GHS: PubChem
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ^ DEA Chemical Handler's Manual: A Guide to Chemical Control Regulations (2022 ed.). United States Department of Justice Drug Enforcement Administration Office of Diversion Control. May 9, 2014.
  4. ^ Schulz W. "Fentanyl". List of Top Pharmaceuticals. Chemical & Engineering News.

Further reading

  • Beckett AH, Casy AF, Kirk G (February 1959). "Alpha- and beta-prodine type compounds". Journal of Medicinal and Pharmaceutical Chemistry. 1 (1): 37–58. doi:10.1021/jm50002a004. PMID 13655028. S2CID 42058755.