p-Toluenesulfonic acid → Methyl 4-amino-3-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a stirred mixture of 85.6 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate and 240 parts of methanol are added 54.6 parts of benzenemethanamine (exothermic reaction). After stirring for 5 minutes, there are added 0.2 parts of 4-methylbenzenesulfonic acid and the whole is hydrogenated at normal pressure and at normal temperature with 10 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, (about 20 hours), the catalyst is filtered off and the filtrate is evaporated. The residue is distilled, yielding methyl 4-amino-3-methyl-1-piperidinecarboxylate; bp. 136°-140° C. (water-jet).

Provenance & Evidence