Sodium Iodide → (r)-5,11-Dihydro-5-[1-[2-(4-dimethylaminophenyl)ethyl]-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine

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Reaction Conditions

Reaction Steps

(R)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine (Preparation Example 1) (420 mg, 1.5 mmol), 2-(4-dimethylaminophenyl)ethyl tosylate (640 mg, 2 mmol), sodium carbonate (210 mg, 2 mmol) and sodium iodide (30 mg, 0.2 mmol) were added to acetonitrile (20 ml), and the mixture was heated under reflux at 90° C. for 14 hours. The solvent was evaporated under reduced pressure, and the residue was partitioned in ethyl acetate and water. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was treated by the column chromatography and then eluted with dichloromethane and then with dichloromethane/2 M methanolic ammonia (50:1) as the eluents. A suitable fraction was collected, and the solvent was evaporated under reduced pressure to obtain the title compound in the form of a light yellow oil (240 mg, 37%).

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