Triethylamine → 2-(2-(4-Hydroxycyclohexyl)aminoanilin-5-yl)benzoxazole

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Reaction Steps

2-(4-Fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (0.60 g, 2.3 mmol) was added to an acetonitrile (20 mL) solution containing triethylamine (0.70 g, 7.0 mmol) and 4-aminocyclohexanol hydrochloride (0.53 g, 2.5 mmol), and this was heated to reflux for 2 hours with stirring. After the reaction was complete, this was cooled to room temperature, and the crystals precipitated by the addition of water were filtered. After the crystals were washed with water, they were dried under reduced pressure with heating to give crystals that were added to a solution of a solvent mixture of methanol/tetrahydrofuran (1:1, 20 mL) including 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 8 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (0.50 g, 67% yield) as pale red crystals.

Provenance & Evidence