4-(cyclopentyloxy)piperidine synthesis

Yield:933736-13-1 99%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol;ethyl acetate; under 1034.32 Torr;

Steps:

11 4.3 General procedure B: preparation of 4-piperidinyl ethers. Preparation of trans ethyl 4-(piperidin-4-yloxy)cyclohexanecarboxylate (19)

General procedure: To a solution of 1.90g (4.88mmol) of 18 in 25mL of a 1:1 mixture of EtOAc/EtOH was carefully added 150mg of 10% Pd/C. The mixture was hydrogenated at 20psi H₂ for 8-20h or until TLC indicated that all SM had been consumed. The slurry was filtered through a pad of cellulose eluting with EtOAc. The solvent was removed under reduced to provide 1.12g (90%) of 19 as a colorless solid:

References:

Kuethe, Jeffrey T.;Janey, Jacob M.;Truppo, Matthew;Arredondo, Juan;Li, Tao;Yong, Kelvin;He, Shuwen [Tetrahedron,2014,vol. 70,# 30,p. 4563 - 4570]