''N''-Phenethyl-4-piperidinone (NPP) is a derivative of

4-piperidinone 4-Piperidinone is a derivative of piperidine with the molecular formula C5 H9 N O. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Piperidones Piperidones are a class of chemical compounds sharin ...

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, NPP was placed 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

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 Seigfried method (shown below and published on

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) 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. :

Preparation

Uses

References

Further reading