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Eschweiler-Clarke Reaction

The Eschweiler-Clarke Reaction allows the methylation of a primary or secondary amine to the corresponding tertiary amine, using excess formic acid and formaldehyde, avoiding the formation of quaternary ammonium salts. Reaction mechanism: 1. Reaction between the amine and formaldehyde generates an aminoalcohol intermediate. 2. Dehydration delivers an iminium ion. 3. Hydride transfer from the reducing agent to the protonated imine delivers the methylated amine. 4. This process is repeated until a tertiary amine is generated, at which point the reaction stops. References: NROChemistry: https://nrochemistry.com/eschweiler-c... Example #1: Org. Lett. 2019, 21, 705. https://doi.org/10.1021/acs.orglett.8...