Triethylamine → HCID 131717514, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(1-methylethyl)-N-(3-hydroxypropyl)-1,2-benzisoxazole-3-carboxamide (7.80 g), triethylamine (3.05 g), and toluene (200 ml), under a nitrogen atmosphere at 0° C., methanesulfonyl chloride (3.40 g), was added rapidly and the mixture was stirred at 0° C. After 35 mins, 4-(4-fluorobenzoyl)piperidine hydrochloride (7.95 g) and triethylamine (8.71 g) were added, and the mixture was heated under reflux for 16 hrs. The reaction mixture was washed with 10% sodium hydroxide, water, and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel, eluting with 5 to 10% methanol in ethyl acetate. The appropriate fractions were collected and evaporated. A solution of the residue in methanol was acidified with hydrogen chloride-ethanol solution and diluted with ether. The mixture was refrigerated, and the solid was collected. Recrystallization of the solid from ethanol/ethyl acetate afforded 1.50 g (10.2%) of product, mp 177°-179° C.

Provenance & Evidence