Dimethyl Sulfoxide → [3-(5-Fluoro-1H-indol-3-yl)-propyl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methyl)-amine

Participants

Reaction Steps

A solution of 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methylamine (0.45 g, 2.5 mmol) and 5-fluoro-indolyl-3-propylbromide (0.6 g, 2.5 mmol), and triethylamine (0.5 g) in dimethylsulfoxide (20 mL) was heated to 100° C. for 10 hours. The reaction mixture was poured into water (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and the solvent removed under vacuum. Chromatography (10% methanol-methylene chloride) afforded 0.42 g (47%) of desired product as a yellowish brown oil. The oxalate salt was prepared in ethanol: mp 189-190° C.

Provenance & Evidence