rel-(2R,6S)-2,6-Dimethylpiperidine → 1-(2-(2,6-Dimethylpiperidyl)ethoxy)-4-((4-chloronaphthyloxy)methyl)benzene

Participants

Reaction Steps

A stirred mixture of 0.4 grams (0.001 mole) of 2-chloro-1-(4-((4-chloronaphthyloxy)methyl)phenoxy)ethane and 5 mL (0.037 mole) of cis-2,6-dimethylpiperidine was heated to just below reflux for about 72 hours. After this time, the reaction mixture was analyzed by thin layer chromatography (TLC), which indicated the reaction was incomplete. The reaction mixture was concentrated under reduced pressure and subject to column chromatography on silica gel, yielding 0.2 gram of compound 106. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence