Sodium Iodide → (r)-5,11-Dihydro-5-[1-[3-(4-methoxyphenyl)propane-1-yl]-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine

HRID 411968Notes

Reaction equation

HRID 411968 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.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32]Br)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][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:26][CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 127769961-(3-Bromopropyl)-4-methoxybenzeneHCID 69200761(r)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]oxazepine

Product 1

HCID 59062713(r)-5,11-Dihydro-5-[1-[3-(4-methoxyphenyl)propane-1-yl]-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) (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%).

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-f75b5195c1a946d6bb53b85da1b468f8
Source dataset
uspto-grants-2003_05
Patent number
US06562808B1

Reaction notes

Loading…