4-Piperidinone

4-Piperidinone

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Names
IUPAC name Piperidin-4-one
Other names 4-Piperidone Azinanone Azinan-4-one
Identifiers
CAS Number	41661-47-6 N
ChemSpider	31091 Y
Jmol 3D model	Interactive image
InChI InChI=1S/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 Y Key: VRJHQPZVIGNGMX-UHFFFAOYSA-N Y InChI=1/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2 Key: VRJHQPZVIGNGMX-UHFFFAOYAC
SMILES O=C1CCNCC1
Properties
Chemical formula	C5H9NO
Molar mass	99.13 g·mol−1
Boiling point	79 °C (174 °F; 352 K)
Vapor pressure	{{{value}}}
Related compounds
Related compounds	Piperidine; 2-Piperidinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Piperidinone is a derivative of piperidine with the molecular formula C₅H₉NO. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs (e.g., fentanyl).

Piperidones

Piperidones are a class of chemical compounds sharing the piperidone skeleton. A classic named reaction for the synthesis of piperidones is the Petrenko-Kritschenko piperidone synthesis which involves combining an alkyl-1,3-acetonedicarboxylate with benzaldehyde and an amine. This multicomponent reaction is related to the Hantzsch pyridine synthesis.

N-Benzyl-4-piperidone is probably one of the most abundant 4-piperidone. It is used to make carpipramine, clocapramine, Fluspirilene, pipamperone, etc. N-Benzyl-4-piperidone is made when 1 equivalent of benzylamine is condensed with 2 molecules of ethylacrylate and the double conjugate addition product is subject of a Dieckmann cyclization followed by saponification and decarboxylation. Note that the intermediate 3-carboethoxy-N-Benzyl-4-piperidone prior to saponification can be used as a product to make Pimozide, Benperidol and droperidol.

N-Methyl-4-piperidone is used to make dorastine, Propiverine. 1,3-dimethyl-4-piperidone is used to make naranol, etc.

N-Carboethoxy-4-piperidone was used to make Lorcainide.