Sodium Iodide → 5,11-dihydro-5-[2-[N-(3-methoxyphenethyl)-N-methylamino]ethyl]dibenzo [b,e][1,4]oxazepine

HRID 1859472Notes

Reaction equation

HRID 1859472 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.S(O[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:34][O:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][CH2:25][N:2]([CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)[CH3:1]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 130615423-Methoxyphenethyl mesylateHCID 186256155,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine

Product 1

HCID 186255835,11-dihydro-5-[2-[N-(3-methoxyphenethyl)-N-methylamino]ethyl]dibenzo [b,e][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

5,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine (349 mg, 1.37 mmol), 3-methoxyphenethyl mesylate (450 mg, 1.96 mmol), sodium carbonate (208 mg, 1.96 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (25 ml), and they were heated under reflux at 90° C. for 6 hours. The solvent was evaporated under reduced pressure. The obtained residue was distributed in ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and hexane (1:2) and then with dichloromethane as the eluent. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-[N-(3-methoxyphenethyl)-N-methylamino]ethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (275 mg, 52%).

Workup

  1. temperaturewere heated
  2. customThe solvent was evaporated under reduced pressure
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washThe product was eluted with dichloromethane and hexane (1:2)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0aff913d1a2a4e53a484c2e02358b819
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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