Chemistry:Piperylone
From HandWiki
Piperylone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties.[1]
Synthesis
- upright=2
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
- ↑ "Piperylone". Pharmaceutical Manufacturing Encyclopedia. 4 (3rd ed.). William Andrew Publishing. 2007. pp. 167p–168p. ISBN 978-0-8155-1526-5.
- ↑ Jucker E, Ebnother A, Lindenmann AJ, "Pyrazolone derivatives", US patent 2903460, issued 1959-09-08, assigned to Sandoz AG
- ↑ "Über neuartige, basisch substituierte Pyrazolon-Derivate. Untersuchungen über synthetische Arzneimittel. 3. Mitteilung". Helvetica Chimica Acta 42 (4): 1201–1214. 1959. doi:10.1002/hlca.19590420415.
- ↑ "Piperylone". Pharmaceutical Substances. Thieme. https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0123.
 |  |
