Ethanol → (4R)-5,6-Dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine dihydroiodide

HRID 2068531노트

반응식

HRID 2068531 반응식
[I:1][Si](C)(C)C.[CH:6]1[N:10]2[C:11]3[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=3[CH2:13][CH2:14][C@@H:15]([NH:16]C(=O)OCC3C=CC=CC=3)[C:9]2=[N:8][CH:7]=1.C(O)C.CCCCCC.C(O)C>ClCCl>[IH:1].[IH:1].[CH:6]1[N:10]2[C:11]3[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=3[CH2:13][CH2:14][C@@H:15]([NH2:16])[C:9]2=[N:8][CH:7]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 85247Trimethylsilyl iodide2회HCID 21879635Ethanol hexaneHCID 58304077benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate

생성물 1

HCID 67234232(4R)-5,6-Dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine dihydroiodide수율 98.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Add iodotrimethylsilane (783 mL, 5.49 mol) to dichloromethane (800 mL) and cool in an ice water bath. Dissolve benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate (610 g, 1.83 mol) in dichloromethane (1 L) and add to the iodotrimethylsilane solution. After addition is complete, remove the ice water bath and allow the reaction to stir for approximately 16 hours at ambient temperature. Stir a mixture of hexanes (6 L) and ethanol (1 L) in an ice water bath. Add the reaction mixture to the stirring hexane/ethanol mixture carefully to avoid foaming. Stir it at ambient temperature 10 minutes. Remove the resulting solid by filtration and wash the cake with hexanes (3×2 L) to give the title compound (817.1 g, 98%) as an orange, free flowing solid: MS (m/z): 200 (M+1).

후처리

  1. temperaturecool in an ice water bath
  2. additionAfter addition
  3. customremove the ice water bath
  4. customthe reaction
  5. stirringStir
  6. stirringStir it at ambient temperature 10 minutes
  7. customRemove the resulting solid
  8. filtrationby filtration
  9. washwash the cake with hexanes (3×2 L)

출처 및 근거

ORD 기록
ord-b423691cad1645e99d60bd8dfb7ee8e3
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299061B2

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