Triethylamine → N-(1-Methylethyl)-N-[2-(1-(6-fluoro-1,2-benzisoxazol-3-yl)-4-piperadinyl)ethyl]-1,2-benzisoxazol-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, methanesulfonyl chloride (3.70 g) was rapidly added to a solution of N-(1-methylethyl)-N-(2-hydroxyethyl)-1,2-benzisoxazole-3-carboxamide (8.00 g), triethylamine (3.27 g), and tetrahydrofuran (150 ml), at 0° C., and the mixture stirred at 0° C. for 30 mins. To the mixture was added rapidly a suspension of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (7.80 g), triethylamine (6.53 g), and tetrahydrofuran (60 ml), and the mixture was heated under reflux for 12 hrs. Water was added and the solution was concentrated under reduced pressure. The residue was dissolved in dichloromethane (150 ml), washed with 10% sodium hydroxide solution, water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with 80% ethyl acetate in hexanes. The appropriate fractions were collected and evaporated, and the residue was recrystallized from ether to afford 2.33 g (16.0%) of product, mp 118°-120° C.

Provenance & Evidence