Grandberg, I. I. published the artcileDemjanov rearrangement in a series of nitrogenous heterocycles, Application In Synthesis of 14613-37-7, the publication is Doklady TSKhA (1970), 226-31, database is CAplus.
Three isomeric compounds, 2-, 3- and 4-aminomethyl-N-methylpiperidine, were diazotized and the degradation products obtained at 0°, pH 5.5, separated and identified. The 2-substituted derivative gave 2-hydroxymethyl-N-methylpiperidine, 6-methylaminohexan-2-one, 1,2-dimethylpiperidin-2-one, and 2,3-dehydro-1-methylhexamethylenimine in the proportion 49:16:-26:9. The 3-substituted derivative gave 3-hydroxymethyl-N-methylpiperidine, 3(4)-hydroxy-1-methylhexamethylenimine, 1,-3-dimethyl-3-hydroxypiperidine, 2 unsaturated piperidine derivatives (estimated together) and an unsaturated hexamethylenimine derivatives in the proportion 62:2:14:16:6. The ratios of corresponding products with the 4-substituted derivative were 38:1:39:16:6. Two mechanisms based on the conformation of the piperidine ring are proposed to explain the unusually low ratio of rearrangement products and the predominance of H over C atom migration in these reactions.
Doklady TSKhA published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Application In Synthesis of 14613-37-7.
Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem