Triethylamine → HCID 19752291, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, methanesulfonyl chloride (3.70 g) was rapidly added to a solution of N-methyl-N-(2-hydroxyethyl)-1,2-benzisoxazole-3-carboxamide (7.10 g), triethylamine (3.27 g), and tetrahydrofuran (100 ml) at 0° C., and the mixture was stirred at 0° C. for 60 mins. To the mixture was rapidly added a suspension of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (8.10 g), triethylamine (7.26 g), and tetrahydrofuran (80 ml), and the mixture was heated under reflux for 16 hrs. Water was added, and the solution was concentrated under reduced pressure. The residue was diluted with 10% sodium hydroxide solution and extracted with 50% ether-toluene. The combined extracts were washed with water and brine, dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate. The appropriate fractions were collected and evaporated. The residue was recrystallized from ether to afford 3.01 g (22.1%) of product, mp 94°-97° C.

Provenance & Evidence