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

HRID 2251908Notes

Reaction equation

HRID 2251908 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]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:28]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:1][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)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 186256155,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepineHCID 22934159HCID 22934159, compound

Product 1

HCID 129906075,11-dihydro-5-[2-[N-methyl-N-(3-pyrrolidinophenethyl)amino]-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 (254 mg, 1.00 mmol, prepared by a method disclosed in International Patent No. 0040570A1), 3-pyrrolidinophenethyl mesylate (296 mg, 1.10 mmol), sodium carbonate (138 mg, 1.30 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (20 ml), and they were heated at 90° C. under reflux for 6.5 hours. The solvent was evaporated under reduced pressure, and the residue was distributed into 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 the silica gel column chromatography. After the elution with hexane and ethyl acetate (10:1) and then with hexane and ethyl acetate (3:1) as the eluent, suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain 5,11-dihydro-5-[2-[N-methyl-N-(3-pyrrolidinophenethyl)amino]-ethyl]dibenzo[b,e][1,4]oxazepine in the form of a light yellow oily substance (331 mg, 78%).

Workup

  1. temperatureunder reflux for 6.5 hours
  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. washAfter the elution with hexane and ethyl acetate (10:1)
  7. customwith hexane and ethyl acetate (3:1) as the eluent, suitable fractions were collected
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1e9027fa47594318b91d7441d4b20c78
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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