1′‐Methylspiro[3H‐indole‐3,n'‐piperidines] 2 can be obtained from the 1‐methyl‐n‐piperidinecarbaldehydes 1 by the Fischer reaction of their phenylhydrazones. The Fischer reaction provides different kinds of products ‐3H‐indole, indole and oxindole‐ which depend on the N atom position in the piperidine ring.
The reduction of the n‐(1,3‐dioxolan‐2‐yl)‐1‐methylpyridinium ions with sodium borohydride has been studied to prepare N‐methylformylpiperidines. Deuterium oxide was used as the solvent in order to assign the protons in the nmr spectra. As a product of the reaction, the 4‐(1,3‐dioxolan‐2‐yl)‐1‐methyl‐1,2,3,6‐tetrahy‐dropyridine‐borane complex, was isolated and crystallized. A X‐ray study of this borane complex has been carried out.
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