Sulfuric Acid → HCID 17902007, compound

Participants

Reaction Steps

A solution of 97% sulfuric acid (79 mg) in tetrahydrofuran (0.5 mL) was added to a mixture of 2-amino-5-bromo-N-(3-chloro-4-methoxybenzyl)benzamide (199 mg), cyclopentanone (68 mg) and sodium borohydride (31 mg) in tetrahydrofuran (3 mL). The mixture was stirred for an hour at ambient temperature. Then cyclopentanone (68 mg), sodium borohydride (31 mg) and a solution of 97% sulfuric acid (80 mg) in tetrahydrofuran (0.5 mL) were added to the reaction mixture. After stirring for additional 2 hours at ambient temperature, the reaction mixture was diluted with water. The resultant was made alkaline with an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a preparative silica gel thin layer chromatography developed by 25% ethyl acetate in hexane. The obtained substance was dissolved in diethyl ether, and 4 N-hydrogen chloride solution in ethyl acetate (0.3 mL) was added thereto. The mixture was concentrated in vacuo and the residue was triturated with diethyl ether to give 5-bromo-N-(3-chloro-4-methoxybenzyl)-2-(cycloperitylamino)benzamide hydrochloride (198 mg) as white powders.

Provenance & Evidence