N-Phenethyl-4-piperidinone

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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 Edit this at Wikidata
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 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
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]
GHS07: Exclamation mark
Warning
H302
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).
checkY verify (what is checkYX markN ?)
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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 addictive drugs, 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.

There are a handful of other uses (although less common):

  1. PD180787
  2. Propinetidine
  3. Fenspiride
  4. Capeserod
  5. PEPAP

References

Further reading

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