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

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).

1. filtrationThe reaction was filtered
2. customthe solvent evaporated
3. customto afford a yellow gum
4. filtrationfiltered
5. customThe solvent was removed
6. customto afford an orange oil
7. distillationthis was purified by distillation at 1.0 mBar
8. customcollecting fractions
9. distillationthat distilled at 70° C.

ORD record

ord-0e7d158fcb224602b0ef14a83c6bd0fb

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2