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

HRID 2068531Notes

Reaction equation

HRID 2068531 reaction equation
[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

Participants

6

Reactant 4

HCID 702EthanolHCID 85247Trimethylsilyl iodide2×HCID 21879635Ethanol hexaneHCID 58304077benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b423691cad1645e99d60bd8dfb7ee8e3
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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