Piperylone
(Redirected from Piperylon)
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| ECHA InfoCard | 100.017.990 |
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| Formula | C17H23N3O |
| Molar mass | 285.391 g·mol−1 |
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Piperylone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties.[1]
Synthesis
[edit]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
[edit]- ↑ "Piperylone". Pharmaceutical Manufacturing Encyclopedia. Vol. 4 (3rd ed.). William Andrew Publishing. 2007. pp. 167p–168p. ISBN 978-0-8155-1526-5.
- ↑ US patent 2903460, Jucker E, Ebnother A, Lindenmann AJ, "Pyrazolone derivatives", issued 1959-09-08, assigned to Sandoz AG
- ↑ 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.
- ↑ "Piperylone". Pharmaceutical Substances. Thieme. Retrieved 2024-07-17.
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