Sodium Iodide → 5-[2-[N-(4-chlorophenethyl)-N-methyl-amino]ethyl]-5,11-dihydrodibenzo[b,e][1,4]oxazepine

HRID 1859476노트

반응식

HRID 1859476 반응식
[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][C:30]([Cl:33])=[CH:29][CH:28]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[Cl:33][C:30]1[CH:31]=[CH:32][C: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:28][CH:29]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 129420784-Chlorophenethyl mesylateHCID 186256155,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine

생성물 1

HCID 186256005-[2-[N-(4-chlorophenethyl)-N-methyl-amino]ethyl]-5,11-dihydrodibenzo[b,e][1,4]oxazepine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

5,11-Dihydro-5-[2-(N-methylamino)ethyl]dibenzo[b,e][1,4]oxazepine (254 mg, 1.00 mmol), 4-chlorophenethyl mesylate (352 mg, 1.50 mmol), sodium carbonate (160 mg, 1.50 mmol) and sodium iodide (20 mg, 0.13 mmol) were added to acetonitrile (25 ml), and they were heated at 70° C. under stirring for 22 hours and then at 90° C. under reflux 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 then with dichloromethane and methanol (100:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain 5-[2-[N-(4-chlorophenethyl)-N-methyl-amino]ethyl]-5,11-dihydrodibenzo[b,e][1,4]oxazepine in the form of a light yellow oil (171 mg, 44%).

후처리

  1. temperatureat 90° C. under reflux for 6 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. washThe product was eluted with dichloromethane
  7. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-9feb4dec620b42fcb3cb35fa0cc84a0b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528504B2

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