''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 In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

C₁₃H₁₇NO. It is used as an intermediate in the manufacture of chemicals and

pharmaceutical drug A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ...

s such as

fentanyl Fentanyl, also spelled fentanil, is a very potent synthetic opioid used as a pain medication. Together with other drugs, fentanyl is used for anesthesia. It is also used illicitly as a recreational drug, sometimes mixed with heroin, cocaine ...

. 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 catalyst In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of heterogeneous catalysis. Ionic reac ...

Uses

''N''-Phenethyl-4-piperidinone is useful in the synthesis of pharmaceuticals, primarily fentanyl and its analogs.

Paul Janssen Paul Adriaan Jan, Baron Janssen (12 September 1926 - 11 November 2003) was a Belgian physician. He was the founder of Janssen Pharmaceutica, a pharmaceutical company with over 20,000 employees which is now a subsidiary of Johnson & Johnson. Ea ...

(founder of

Janssen Pharmaceutica Janssen Pharmaceuticals is a pharmaceutical company headquartered in Beerse, Belgium, and wholly-owned by Johnson & Johnson. It was founded in 1953 by Paul Janssen. In 1961, Janssen Pharmaceuticals was purchased by New Jersey-based American c ...

) first synthesized fentanyl in 1960 from

Benzylfentanyl Benzylfentanyl (R-4129) is a fentanyl analog. It was temporarily placed in the US Schedule I by emergency scheduling in 1985 due to concerns about its potential for abuse as a designer drug, but this placement was allowed to expire and benzylfen ...

. The Seigfried 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 Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds appli ...

to 4-anilino-''N''-phenethylpiperidine (ANPP). This product is reacted with propionyl chloride to form

. :

Preparation

Uses

References

Further reading