J. Caldwell, I. Collins
Sep 1, 2006
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Abstract
Rapid synthesis of 4-benzyl-4-aminopiperidines by addition of Grignard reagents to N-(1-Boc-piperidin-4-ylidene)-tert-butanesulfinyl imine Two concise methods for the synthesis of aryl-substituted 4-benzyl-4-aminopiperidines by the addition of benzyl Grignard reagents to sulfinyl imines were developed. The hydration-prone tert-butanesulfinyl imine derived from N-Boc-piperidin-4-one was trapped as a stable alpha-(N-sulfinyl)aminonitrile, which underwent displacement of the nitrile on treatment with Grignard reagents. Alternatively, benzyl and allyl Grignards added to the sulfinyl imine in situ in a one-pot procedure. Acid deprotection provided various substituted 4-benzyl-4-aminopiperidines.