Sodium Iodide → Dibenzo[b,e][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

(R)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine (Preparation Example 1) (220 mg, 0.78 mmol), 2-[4-(N-t-butoxycarbonylamino)phenyl]ethyl chloride (400 mg, 1.02 mmol), sodium carbonate (110 mg, 1.02 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (15 ml), and the mixture was heated under reflux at 90° C. for 15 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 (R)-5,11-dihydro-5-[1-[2-(4-N-t-butoxycarbonylamino)phenyl)ethyl]-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (380 mg, 97%).

Provenance & Evidence