When anabasine is treated with 30% hydrogen peroxide in acetic acid, both the pyridine and piperidine parts of the molecule of this alkaloid are oxidized with formation of δ-(hydroxyimino)-3-pyridinevaleric acid 1-oxide, whose structure was established by studying its reactions and comparing it with a synthetic sample.
Reduction of δ-(hydroxyimino)-3-pyridinevaleric acid 1-oxide gives (±)-δ-amino-3-pyridinevaleric acid lactam.
The action of 10% aqueous hydrogen peroxide is directed at the piperidine nitrogen atom of the anabasine molecule; as a result of the subsequent transformations the piperidine nucleus undergoes cleavage with formation of δ-(hydroxyimino)-3-pyridinevaleric acid.
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The authors find it a pleasant duty to thank J. Kovar (Prague) for the sample of 6-oxo-3-pyridinevaleric acid and for describing the method by which it was prepared.
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Gol'dfarb, Y.L., Alashev, F.D. & Zvorykina, V.K. Oxidation of anabasine with hydrogen peroxide. Russ Chem Bull 11, 2112–2117 (1962). https://doi.org/10.1007/BF00911374
- Hydrogen Peroxide
- Acetic Acid