Formaldehyde → 1,4-Dimethylpiperidine-4-carboxylic acid

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Reaction Steps

4-Methyl isonipecotic acid (5.10 g, 35 mmol) was placed in a Parr flask and diluted with 400 mL H2O. 10 mL of a 30% formaldehyde solution was added followed by 5.0 g of 10% Pd/C. The reaction mixture was hydrogenated at 50 psi overnight, filtered through celite, washed with H2O, and evaporated. HPLC 1:1 methanol/dichloromethane containing 2% acetic acid afforded 1,4-dimethylpiperidine-4-carboxylic acid. (0.859 g, 15%). 1H NMR (200 MHz DMSO d6) δ3.0 (m, 2H), 2.5 (m, 2H), 2.4 (s, 3H), 2.1 (m, 2H), 1.5 (m, 2H), 1.1 (s, 3H).

Provenance & Evidence