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

HRID 1859474Notes

Reaction equation

HRID 1859474 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][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][CH2:25][N:2]([CH2:3][CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][O:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH3:1])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 116659383-(4-Methoxyphenyl)propyl methanesulfonateHCID 186256155,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine

Product 1

HCID 186255905,11-dihydro-5-[2-[N-[3-(4-methoxyphenyl)propyl]-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 (245 mg, 0.96 mmol), 3-(4-methoxyphenyl)propyl mesylate (353 mg, 1.45 mmol), sodium carbonate (154 mg, 1.45 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 residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and hexane (1:2) and then with dichloromethane. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-[N-[3-(4-methoxyphenyl)propyl]-N-methylamino]ethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (101 mg, 26%).

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-a3d6e5b6bd4146909835172ec9dec556
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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