Formic Acid → (1-Methyl-3-piperidyl)methanol

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Reaction Steps

A! At 0° C., 3-hydroxymethyl-piperidine (20 g, 173 mmoles) was slowly added to formic acid (63 ml, 1.66 moles) then a 40% solution of formaldehyde was added (62.4 ml, 833 mmoles). The mixture was refluxed for 5 hours, then the solvent was evaporated and the residue taken up in little water, brought to basic pH with 32% sodium hydroxide and extracted with ethyl ether. The organic phase was anhydrified over sodium sulfate and evaporated. The resultant crude was purified by distillation and provided 17 g (yield: 76%) of N-methyl-3-hydroxymethylpiperidine (b.p.--85°-86° C./1 mmHg).

Provenance & Evidence