N-Phenethyl-4-piperidinone (NPP) Cas 39742-60-4
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Description
Description of N-Phenethyl-4-piperidinone (NPP) Cas 39742-60-4
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.
| N-Phenethyl-4-piperidinone | |
|---|---|
| IUPAC name | 1-(2-Phenylethyl)piperidin-4-one |
| Other names | N-Phenethyl-4-piperidinone |
| Abbreviations | NPP |
| Identifiers | |
| CAS number | |
| SMILES | C1CN(CCC1=O)CCC2=CC=CC=C2 |
| Properties | |
| Molecular formula | C13H17NO |
| Molar mass | 203.28 g mol-1 |
| Hazards | |
| EU classification | Flammable (F) Harmful (Xn) Dangerous for the environment (N) |
| NFPA 704 |
3
1
0
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.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.
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