Potassium Carbonate → Phthalimide

HRID 1769670Notes

Reaction equation

HRID 1769670 reaction equation
CNCC(C1C=CC(OC)=C(OC)C=1)C.BrCCC[N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:24]1(=[O:25])[NH:20][C:21](=[O:30])[C:22]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 14089103HCID 14089103, compound

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.55 g of N-methyl-N-(2-(3,4-dimethoxyphenyl)propyl)amine, 1.98 g of N-(3-bromopropyl)phthalimide, 1.0 g of anhydrous potassium carbonate and 10 ml of acetonitrile was refluxed under heating for 6 hours. They were allowed to cool and then concentrated after filtering out insoluble matters. The residue was purified on silica gel column chromatography (solvent: chloroform:methanol=100:1), to obtain 2.71 g of N-(3-(N'-(2-(3,4-dimethoxyphenyl)propyl)-N'-methyl)amino)propyl)phthalimide as yellow oil. The product was dissolved in 20 ml of ethanol, to which 0.4 ml of hydrazine monohydrate was added and refluxed under heating for 2 hours. Deposited matters were filtered out and diluted aqueous solution of sodium hydroxide was added, which was extracted with chloroform. After drying with anhydrous sodium sulfate, the solvent was distilled off and the residue was purified on silica gel column chromatography (solvent: chloroform:methanol:concentrated aqueous ammonia: 100:10:1) to obtain 1.54 g of the above-captioned compound as yellow oil (yield: 78%).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 6 hours
  3. temperatureto cool
  4. concentrationconcentrated
  5. filtrationafter filtering out insoluble matters
  6. customThe residue was purified on silica gel column chromatography (solvent: chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-a21add22db0940b7a3d031430dea36cb
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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