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N-Phenethyl-4-piperidinone

CAS number 39742-60-4



N-Phenethyl-4-piperidinone IUPAC name
1-(2-Phenylethyl)piperidin-4-one
Other names N-Phenethyl-4-piperidinone
Abbreviations NPP

Identifiers

CAS number [39742-60-4]
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)

N-Phenethyl-4-piperidinone (NPP) is a derivative of 4-piperidinone with the molecular formula C13H17NO. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs such as fentanyl.

Because of its use in the illicit manufacture of fentanyl, NPP was placed onto the list of controlled chemicals in the USA in 2007, and possession and sales of this compound are now heavily restricted.

Chemistry

Synthesis:

* 4-piperidinone hydrochloride was first reacted with phenethyl bromide to give N-phenethyl-4-piperidinone (NPP).
* Treatment of the NPP intermediate with aniline.
* Reduction with sodium borohydride afforded 4-anilino-N-phenethyl-piperidine (ANPP).
* A final acylation reaction between ANPP and propionic anhydride led to the fentanyl.

Analogues: Alfentanil

* Opioid analgesic (painkiller) with rapid onset of action
* Used for surgery
* Injectable alfentanil marketed under brand name Alfenta
* Can last around 30 minutes

Carfentanil

* Marked under the name Wildnil as a tranquilizer for large animals
* 10,000 times stronger than morphine
* 100 times stronger than fentanyl
* Discovered by Janssen Pharmaceutica

Remifentanil

* Opioid analgesic (painkiller) marked under the name Ultiva
* Extremely rapid onset and offset
* Blood concentration decreases by 50% in 3-6 minutes after a one-minute infusion of remifentanil

Sufentanil

* 5-10 times more potent than fentanyl
* Marketed as Sufenta and Sufentil
* Sometimes used during anesthesia
* Transdermal patch for chronic pain sufferers currently in development

A narcotic analgesic used in combination with other drugs before, during, or following surgery and also for chronic pain management.

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