Potassium Iodide → 3-(N-acetyl-N-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-amino)benzoic acid ethyl ester

HRID 1737225

반응식

HRID 1737225 반응식
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[I-].[K+].[CH2:22]([O:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=1)[CH3:23].[H-].[Na+]>C(C(C)=O)C.CS(C)=O.O>[CH2:22]([O:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([C:33](=[O:35])[CH3:34])[CH2:2][CH2:3][CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH:27]=1)[CH3:23]

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 700589Ethyl 3-acetamidobenzoate

생성물 1

HCID 701960133-(N-acetyl-N-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-amino)benzoic acid ethyl ester

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

A mixture of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine (1.5 g, 0.0055 mol, prepared similarly as described in example 2) and potassium iodide (5.4 g, 0.0327 mol) in methyl ethyl ketone (100 ml) was heated at reflux temperature for 1 h and then stirred at room temperature overnight. The mixture was filtered and the solvent evaporated in vacuo. The crude halogenide was dissolved in dry dimethyl sulfoxide (15 ml) and kept. A solution of 3-acetylaminobenzoic acid ethyl ester (1.5 g, 7.4 mmol) in dry dimethyl sulfoxide (15 ml) was heated to 50° C. and sodium hydride (0.32 g, 8.1 mmol, 60% oil dispersion) was added in portions. The resulting mixture was heated at 120° C. for 2.5 h, and the mixture was allowed to cool to 80° C. before the above solution containing the halogenide was added. The resulting mixture was heated at 115-120° C. overnight and then allowed to cool to room temperature. Water (100 ml) was added and the resulting mixture was extracted with dichloromethane (3×200 ml). The organic extracts were discarded and pH of the aqueous phase was adjusted to 7. The aqueous phase was extracted with ethyl acetate (100 ml) and dichloromethane (2×100 ml), and the combined organic extracts were dried (MgSO4). The volatiles were removed in vacuo to give a residue which was purified by flash chromatography on silica gel (200 g) using ethyl acetate as eluent, affording 1.0 g of 3-(N-acetyl-N-(3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-amino)benzoic acid ethyl ester as an oil.

후처리

  1. customprepared similarly
  2. temperaturewas heated
  3. temperatureat reflux temperature for 1 h
  4. filtrationThe mixture was filtered
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe crude halogenide was dissolved in dry dimethyl sulfoxide (15 ml)
  7. temperatureThe resulting mixture was heated at 120° C. for 2.5 h
  8. temperatureto cool to 80° C. before the above solution
  9. additioncontaining the halogenide
  10. additionwas added
  11. temperatureThe resulting mixture was heated at 115-120° C. overnight
  12. temperatureto cool to room temperature
  13. extractionthe resulting mixture was extracted with dichloromethane (3×200 ml)
  14. extractionThe aqueous phase was extracted with ethyl acetate (100 ml) and dichloromethane (2×100 ml)
  15. dry with materialthe combined organic extracts were dried (MgSO4)
  16. customThe volatiles were removed in vacuo
  17. customto give a residue which
  18. customwas purified by flash chromatography on silica gel (200 g)

출처 및 근거

ORD 기록
ord-c443319f5c53439ebc12c26a7e1ef713
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962449

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