Piperylone Explained

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]

Notes and References

  1. Book: Pharmaceutical Manufacturing Encyclopedia . 3rd . . 2007 . 978-0-8155-1526-5 . 4 . 167p–168p . Piperylone .
  2. US . 2903460 . Jucker E, Ebnother A, Lindenmann AJ . Pyrazolone derivatives . patent . 1959-09-08 . 1958-12-09 . Sandoz AG.
  3. 10.1002/hlca.19590420415 . Über neuartige, basisch substituierte Pyrazolon-Derivate. Untersuchungen über synthetische Arzneimittel. 3. Mitteilung . 1959 . Ebnöther A, Jucker E, Lindenmann A . Helvetica Chimica Acta . 42 . 4 . 1201–1214 .
  4. Web site: Piperylone . Pharmaceutical Substances . Thieme . 2024-07-17 .

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