Piperylone

Chemical compound From Wikipedia, the free encyclopedia

Piperylone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties.[1]

CAS Number
Quick facts Identifiers, CAS Number ...
Piperylone
Identifiers
  • 4-ethyl-2-(1-methylpiperidin-4-yl)-5-phenyl-1H-pyrazol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.017.990 Edit this at Wikidata
Chemical and physical data
FormulaC17H23N3O
Molar mass285.391 g·mol−1
3D model (JSmol)
  • CCC1=C(NN(C1=O)C2CCN(CC2)C)C3=CC=CC=C3
  • InChI=1S/C17H23N3O/c1-3-15-16(13-7-5-4-6-8-13)18-20(17(15)21)14-9-11-19(2)12-10-14/h4-8,14,18H,3,9-12H2,1-2H3
  • Key:LBFGQUCAQWAFNN-UHFFFAOYSA-N
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Synthesis

Hydrazone formation of 1-methyl-4-piperidone (1) with benzohydrazide (2) gives (3). Catalytic hydrogenation using Adams' catalyst gives the substituted hydrazine (6) after acid-catalyzed hydrolysis to remove the benzoyl group and neutralization. The pyrazolone ring is formed in a condensation reaction with ethyl 2-benzoylbutanoate (7), yielding piperylone.[2][3][4]

References

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