2-Pyridinemethanamine → 2,5-Bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide

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Reaction Steps

To a solution of 8.93 g (2.5 mmole) of compound (II) in 80 mL of ethyl acetate under argon, 2-(aminomethyl)pyridine (3.2 g, 3.0 mmole) were added with stirring and the mixture was refluxed for 4 hours. An additional 1 g of 2-(aminomethyl)pyridine was added and the mixture was refluxed for two more hours. The ethyl acetate was evaporated under reduced pressure and the residue was passed through a 12 cm column containing silica gel with a mixture of methylene chloride:hexane (1:1) as eluent. The column was washed with methylene chloride and the combined solutions were evaporated under reduced pressure. The residue was crystallized from CH2CI2:hexane (1:2) to give 7 g (69% yield) of 2,5-bix(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide (V) m.p. 104-106° C., purity 99.8% (GC).

Provenance & Evidence