Toluene → 2-[2-(Methyl-2-propyn-1-ylamino)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 374564Notes

Reaction equation

HRID 374564 reaction equation
BrCC[C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8].[CH3:15][NH:16][CH2:17][C:18]#[CH:19].C(=O)([O-])[O-].[K+].[K+].[C:26]1(C)C=CC=C[CH:27]=1>>[CH3:15][N:16]([CH2:17][C:18]#[CH:19])[CH2:26][CH2:27][N:9]1[C:10](=[O:11])[C:5]2[C:6](=[CH:12][CH:13]=[CH:14][CH:4]=2)[C:7]1=[O:8]

Participants

5

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 96160N-methylpropyn-2-ylamineHCID 219600212-Bromoethylphthalimide

Product 1

HCID 158138762-[2-(Methyl-2-propyn-1-ylamino)ethyl]-1H-isoindole-1,3(2H)-dione

Procedure

A mixture of bromoethylphthalimide (20.23 g, 0.080 mol), N-methyl-N-propargyl amine (5.0 g, 0.072 mol), potassium carbonate (17.5 g, 0.126 mol), and toluene (80 ml) was refluxed for 8 hours, filtered and the insoluble material washed with toluene. After removal of the solvent, the residue was purified by flash chromatography (Merck 60 silica gel, step gradient from pure dichloromethane to 4% methanol in dichloromethane). The pure fractions were combined, evaporated under reduced pressure, dried in vacuo to provide 16.24 g of title product.

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationfiltered
  3. washthe insoluble material washed with toluene
  4. customAfter removal of the solvent
  5. customthe residue was purified by flash chromatography (Merck 60 silica gel, step gradient from pure dichloromethane to 4% methanol in dichloromethane)
  6. customevaporated under reduced pressure
  7. customdried in vacuo

Sources & evidence

ORD record
ord-96c46db709814b218cbb034d748a698a
Source dataset
uspto-grants-1996_01
Patent number
US05480988

Reaction notes

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