Benzyl Bromide → HCID 18317750, compound

HRID 1700434Notes

Reaction equation

HRID 1700434 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[CH2:17][C:16]3[NH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:18])[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:15]1[C:16]2[CH2:17][CH:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:10][C:11](=[O:18])[C:12]=2[CH:13]=[CH:14]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11052946HCID 11052946, compound

Product 1

HCID 18317750HCID 18317750, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.18 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.8 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added a solution of benzyl bromide (0.71 g) in dimethylformamide (3 ml), and the mixture was stirred at the same temperature for 2.5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) and recrystallized from ethyl acetate-isopropylether to give colorless crystals of 1-benzyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.86 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 2.5 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  8. customrecrystallized from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-e87d2a96c37b4ae0a2575ceb092381c3
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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