Sodium Iodide → (r)-5,11-Dihydro-5-[1-[3-(4-methoxyphenyl)propane-1-yl]-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) (280 mg, 1.0 mmol), 3-(4-methoxyphenyl)-1-propyl bromide (320 mg, 1.4 mmol), sodium carbonate (150 mg, 1.4 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (20 ml), and the mixture was heated under reflux at 90° C. for 13 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 as the eluent. 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 (310 mg, 72%).

Provenance & Evidence