Piperylone

Piperylone

Identifiers
IUPAC name 4-ethyl-2-(1-methylpiperidin-4-yl)-5-phenyl-1H-pyrazol-3-one
CAS Number	2531-04-6
PubChem CID	17319
ChemSpider	16389
UNII	XWH5VH1L2F
CompTox Dashboard (EPA)	DTXSID90179956
ECHA InfoCard	100.017.990
Chemical and physical data
Formula	C17H23N3O
Molar mass	285.391 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC1=C(NN(C1=O)C2CCN(CC2)C)C3=CC=CC=C3
InChI 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

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

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

1. "Piperylone". Pharmaceutical Manufacturing Encyclopedia. Vol. 4 (3rd ed.). William Andrew Publishing. 2007. pp. 167p –168p. ISBN   978-0-8155-1526-5.
2. USpatent 2903460,Jucker E, Ebnother A, Lindenmann AJ,"Pyrazolone derivatives",issued 1959-09-08, assigned to Sandoz AG 
3. Ebnöther A, Jucker E, Lindenmann A (1959). "Über neuartige, basisch substituierte Pyrazolon-Derivate. Untersuchungen über synthetische Arzneimittel. 3. Mitteilung". Helvetica Chimica Acta. 42 (4): 1201–1214. doi:10.1002/hlca.19590420415.
4. "Piperylone". Pharmaceutical Substances. Thieme. Retrieved 2024-07-17.