Sodium Iodide → 5,11-dihydro-5-[2-[N-(3-methoxyphenethyl)-N-methylamino]ethyl]dibenzo [b,e][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

5,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine (349 mg, 1.37 mmol), 3-methoxyphenethyl mesylate (450 mg, 1.96 mmol), sodium carbonate (208 mg, 1.96 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 hours. The solvent was evaporated under reduced pressure. The obtained residue was distributed in ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and hexane (1:2) and then with dichloromethane as the eluent. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-[N-(3-methoxyphenethyl)-N-methylamino]ethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (275 mg, 52%).

Provenance & Evidence