Methyl iodide → HCID 67339653, compound

HRID 910127Notes

Reaction equation

HRID 910127 reaction equation
[H-].[Na+].[CH2:3]1[N:14]2[C:15]3[CH:7]([CH2:8][CH2:9][C:10](=[O:16])[C:11]=3[CH:12]=[CH:13]2)[CH2:6][NH:5][CH2:4]1.I[CH3:18]>CN(C)C=O>[CH3:18][CH:9]1[CH2:8][CH:7]2[CH2:6][NH:5][CH2:4][CH2:3][N:14]3[C:15]2=[C:11]([CH:12]=[CH:13]3)[C:10]1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67338376HCID 67338376, compound

Product 1

HCID 67339653HCID 67339653, compoundYield 731.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (0.78 g, 1.9 mmol, 60% in mineral oil) to 1,2,4,5-tetrahydro-6H-[1,4]diazepino[6,7,1-hi]indol-7-one (3.05 g, 1.62 mmol) in dry dimethylformamide (77 mL). Stir for 30 minutes at room temperature and then add iodomethane (2.0 mL, 3.2 mmol). Stir at room temperature for 134 minutes. Partition between ethyl acetate (1 L) and water (500 mL). Wash the organic phase with saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to chromatography (pre-packed silica gel), eluting with a gradient: 1:0-9:1 ethyl acetate/methanol to provide the desired compound (2.42 g, 74%) as an off-white solid.

Workup

  1. stirringStir at room temperature for 134 minutes
  2. customPartition between ethyl acetate (1 L) and water (500 mL)
  3. washWash the organic phase with saturated aqueous sodium chloride
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under reduced pressure
  6. washeluting with a gradient

Sources & evidence

ORD record
ord-d6d636926d3144cf9471ce707cd34723
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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