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

HRID 1859469Notes

Reaction equation

HRID 1859469 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][O:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)(=O)=O)=CC=1.[CH3:29][NH:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:40][O:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][CH2:31][N:30]([CH2:12][CH2:13][N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][O:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)[CH3:29])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 1047354-Methoxy-N-methylbenzeneethanamineHCID 186255895,11-Dihydro-5-[2-(4-methylphenylsulfonyl)oxyethyl]dibenzo [b,e][1,4]oxazepine

Product 1

HCID 186255925,11-dihydro-5-[2-[N-(4-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-(4-methylphenylsulfonyl)oxyethyl]dibenzo [b,e][1,4]oxazepine (650 mg, 1.65 mmol), N-methyl-4-methoxyphenethylamine (290 mg, 1.76 mmol), sodium carbonate (195 mg, 1.84 mmol) and sodium iodide (25 mg, 0.17 mmol) were added to acetonitrile (20 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 ethyl acetate and hexane (6:1) and then with the same solvents (1:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-[N-(4-methoxyphenethyl)-N-methylamino]ethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (423 mg, 66%).

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 ethyl acetate and hexane (6:1)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2a4cce4ecbca41098468f888c37a69b2
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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