Water → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-oxo-2-(2-trifluoroacetylaminophenyl)ethyl]piperidine

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Reaction Conditions

Reaction Steps

482 mg of 2-bromo-N-(trifluoroacetyl)aniline was dissolved in a mixed solvent of 1.8 ml of tetrahydrofuran and 1.8 ml of diethyl ether, and a 1.14M methyllithium diethyl ether solution was added dropwise thereinto at 0° C. After stirring for 10 minutes, the mixture was slowly charged by a cannular to a solution of 2.4 ml of 1.51 M tert-butyllithium and 4 ml of a diethyl ether solution cooled at −78° C. The mixture was stirred for 1 hour. Then, a mixed solution of 500 mg of N1-methoxy,N1-ethyl-2-[1-(2-methoxy-3-pyridyl)methyl]-4-piperidyl]acetamide obtained in Example 55 and 2 ml of tetrahydrofuran was added dropwise thereinto, and the mixture was further stirred for 20 minutes. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate), to give 150 mg of the above compound as a yellow oil.

Provenance & Evidence