4-Piperidone
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477223453
| Name = 4-Piperidone
| ImageFile = Piperidin-4-one-2D-skeletal.png
| PIN = Piperidin-4-one
| OtherNames = 4-Piperidone
Azinanone
Azinan-4-one
| ImageSize = 80px
| ImageFile1 = Piperidin-4-one-3D-balls.png
| ImageSize1 = 150px
| Section1 = {{Chembox Identifiers
| SMILES = O=C1CCNCC1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 31091
| EINECS = 255-481-1
| PubChem = 33721
| InChI = 1/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2
| InChIKey = VRJHQPZVIGNGMX-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H9NO/c7-5-1-3-6-4-2-5/h6H,1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VRJHQPZVIGNGMX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 41661-47-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 15WP1EA7UH
}}
| Section2 = {{Chembox Properties
| C=5 | H=9 | N=1 | O=1
| Density =
| Solubility =
| Solvent = ethanol
| SolubleOther =
| MeltingPt =
| BoilingPtC = 79
| Viscosity =
}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| FlashPtC = 91
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R =
}}
| Section8 = {{Chembox Related
| OtherCompounds = Piperidine; 2-Piperidinone
}}
}}
4-Piperidone is an organic compound with the molecular formula {{chem2|OC(CH2)4NH}}. It can be viewed as a derivative of piperidine. 4-Piperidone is used as an intermediate in the manufacture of chemicals and pharmaceutical drugs. Substituted and dehydro derivatives of 4-piperidinone are intermediates in alkaloid syntheses.{{cite journal |doi=10.1016/s0040-4020(03)00295-3 |title=Recent advances in the synthesis of piperidones and piperidines |date=2003 |last1=Weintraub |first1=Philip M. |last2=Sabol |first2=Jeffrey S. |last3=Kane |first3=John M. |last4=Borcherding |first4=David R. |journal=Tetrahedron |volume=59 |issue=17 |pages=2953–2989 }}
The N-protonated derivative is typically isolated as the hydrate {{chem2|(HO)2C(CH2)4NH2+}}.{{cite journal |doi=10.1002/anie.201408278 |title=Cation-Cation Pairing by N-C-H⋅⋅⋅O Hydrogen Bonds |date=2015 |last1=Gamrad |first1=Waltraud |last2=Dreier |first2=Angelika |last3=Goddard |first3=Richard |last4=Pörschke |first4=Klaus-Richard |journal=Angewandte Chemie International Edition |volume=54 |issue=15 |pages=4482–4487 |pmid=25712229 }}
It is a List I chemical in the United States as it is a precursor to fentanyl.
