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

HRID 411967Notes

Reaction equation

HRID 411967 reaction equation
N1CCC[C@@H]1C[N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][O:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.C(OC(NC1C=CC(CCCl)=CC=1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH:17]1[C:12]2[C:13](=[N:7][C:8]3[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=3[O:10][CH:11]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 185347742-[4-(N-t-butoxycarbonylamino)phenyl]ethyl chlorideHCID 69200761(r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

Product 1

HCID 21955449Dibenzo[b,e][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

(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%).

Workup

  1. temperaturethe mixture was heated
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned in ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionThe residue was treated by the column chromatography
  8. washeluted with dichloromethane as the eluent
  9. customA suitable fraction was collected
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ad6b1780c8b4afb8adbc9bfa8e99d2c
Source dataset
uspto-grants-2003_05
Patent number
US06562808B1

Reaction notes

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