The extension of either the well-known Schmidt reaction (1) or the Beckmann rearrangement (2) to 4-piperidones or their oximes should result in the synthesis of 5-homopiperazinones.Triacetonamine or 2,2,6,6-tetramethyl-4-piperidone (I) was prepared from phorone by the procedure described by Guareschi (3). When the amino ketone, I, was treated with hydrazoic and sulfuric acids, 2,2,7,7-tetramethyl-5-homopiperazinone (II) was formed in a yield of 88%. The following equation illustrates this and subsequent Schmidt reactions:
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