p-Toluenesulfonic acid monohydrate → HCID 58513608, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (Step C, 11.2 g, 33.0 mmol) and p-toluenesulfonic acid monohydrate (6.29 g, 33.0 mmol) in toluene (240 mL) was stirred at reflux temperature for 20 h with Dean-Stark apparatus. The mixture was cooled to 0° C. and a precipitate formed. The precipitate was collected by filtration washing with ethyl acetate. The precipitate was dissolved in ethyl acetate (200 mL) and saturated sodium hydrogencarbonate aqueous solution (100 mL). The organic layer was separated, washed with brine (20 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as eluent) to give the title compound (10.1 g, 95%) as a white solid.

Provenance & Evidence