2-Methylpiperidine → 1-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine

Participants

Reaction Steps

Add 2-methylpiperidine (3.55 g, 36.1 mmol) to a solution of methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester (See Intermediate 13)(1.3 g, 3.6 mmol) in anhydrous THF (15 mL). Heat the reaction mixture at reflux overnight and cool to room temperature. Wash the organic material with 1N HCl (50 mL) and extract the aqueous layer with diethyl ether (2×50 mL). Add SN NaOH to the aqueous layer (pH >10) and extract with dichoromethane (2×50 mL). Dry the organic extracts over Na2SO4, filter and concentrate to give 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine (1.32 g, quantitative).

Provenance & Evidence