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

HRID 411965Notes

Reaction equation

HRID 411965 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][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.S(C1C=CC(C)=CC=1)(O[CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:35][N:34]([CH3:36])[C:31]1[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][N:1]2[CH2:5][CH2:4][CH2:3][C@@H:2]2[CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][O:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 185347644-Dimethylaminophenethyl tosylateHCID 69200761(r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

Product 1

HCID 59062716(r)-5,11-Dihydro-5-[1-[2-(4-dimethylaminophenyl)ethyl]-2-pyrrolidinylmethyl]dibenzo[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) (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%).

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
  9. customA suitable fraction was collected
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4579fb236d7f4b9ca02ac28f3791e7a8
Source dataset
uspto-grants-2003_05
Patent number
US06562808B1

Reaction notes

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