1,2-Dichloroethane → HCID 49785199, compound

Participants

Reaction Steps

2,4,6-Trichlorobenzoic acid (0.169 g, 0.750 mmol), EDC (0.144 g, 0.750 mmol) and 1-hydroxybenztriazole (0.115 g, 0.750 mmol) were stirred in dichloromethane (DCM) (5 mL) for 15 minutes. 3-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (100 mg, 0.5 mmol, Intermediate 3) and diisopropylethylamine (0.175 mL, 1.000 mmol) were added and the solution stirred at room temperature for 16 hr. The mixture was diluted with DCM (50 ml) and washed with saturated sodium bicarbonate (25 ml), water (3×25 ml), brine, dried over anhydrous sodium sulfate and concentrated to a crude oil. The crude oil was twice purified by mass-directed automated preparative HPLC to afford an oil. The purified product was dissolved in dichloromethane (3 ml) and treated with 4N HCl in dioxane (500 uL). The solvents were removed in vacuo and the solid tritruated with diethyl ether to afford product 3-phenyl-7-[(2,4,6-trichlorophenyl)carbonyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride (0.018 g, 0.041 mmol, 8.12% yield)

Provenance & Evidence