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NMR proof of a piperidine to pyrrolidine ring contraction during nucleophilic substitution

Products formed in the reaction of 1-(6-acetyl-2-naphthyl)-4- [(4-methylphenyl)sulfonyloxy] methyl-piperidine with spiperone ketal, 8-{; ; 3-[2-(4-fluorophenyl)-1, 3-dioxolan-2-yl]propyl}; ; -1-phenyl-1, 3, 8-triazaspiro[4.5]decan-4-one, at room and elevated temperatures were compared and the respective structure were assigned based on H-1 and C-13 NMR spectra. Piperidine to pyrrolidine ring transformation at elevated temperature is documented.

NMR ; C-13 NMR ; H-1 NMR ; piperidine ; pyrrolidine ; rearrangement

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