4-Toluenesulfonyl chloride → HCID 58923895, compound

Participants

Reaction Steps

Ammonium hydroxide (5 mL) was added with vigorous stirring to a suspension of 10,10-dimethyl-9-(methylsulfonyl)-5-oxido-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline (0.91 g, 2.6 mmol) in dichloromethane (25 mL). p-Toluenesulfonyl chloride (0.50 g, 2.6 mmol) was added in one portion, and the reaction was stirred for four hours at ambient temperature. The organic layer was separated and washed with 1% aqueous sodium carbonate (50 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting orange solid (0.77 g) was recrystallized from 1,2-dichloroethane to provide 10,10-dimethyl-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine as a white powder, mp 227-228° C.

Provenance & Evidence