Benzyl 4-(2-(dimethylamino)ethoxy)piperidine-1-carboxylate → Dimethyl(2-(piperidin-4-yloxy)ethyl)amine

Participants

Reaction Steps

Benzyl 4-(2-(dimethylamino)ethoxy)piperidine-1-carboxylate (84) (4.5 g, 14.69 mmol) and Palladium on carbon 5% (JM Type87L; 0.9 g, 0.21 mmol) in EtOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 50° C. for 3 hours. The reaction was filtered and the solvent evaporated to afford a yellow gum. This was dissolved in diethyl ether (50 mL) and filtered. The solvent was removed to afford an orange oil, this was purified by distillation at 1.0 mBar, collecting fractions that distilled at 70° C. to afford the desired material as a colourless liquid (1.100 g, 55.9%); 1H NMR (400.132 MHz, CDCl3) δ 1.47-1.38 (2H, m), 1.61 (1H, s), 1.93-1.89 (2H, m), 2.27 (6H, s), 2.50 (2H, t), 2.63-2.56 (2H, m), 3.11-3.05 (2H, m), 3.38-3.31 (1H, m), 3.56 (2H, t).

Provenance & Evidence