N,N-Diethylethylenediamine → 2-(2-Diethylaminoethyl)-3-(4-dimethylaminophenyl)isoindolin-1-one

HRID 231857Notes

Reaction equation

HRID 231857 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])O2)=[CH:5][CH:4]=1.C(N(CC)C(=O)C1C=CC=CC=1C(O)C1C=CC(N(C)C)=CC=1)C.[CH2:44]([N:46]([CH2:50][CH3:51])[CH2:47][CH2:48][NH2:49])[CH3:45]>[Cl-].[Zn+2].[Cl-]>[CH2:44]([N:46]([CH2:50][CH3:51])[CH2:47][CH2:48][N:49]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:19])=[CH:8][CH:7]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:18])[CH3:45]

Participants

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 145020423-[4-(Dimethylamino)phenyl]-2-benzofuran-1(3H)-oneHCID 14502043N,N-diethyl-2-[1-hydroxy-1-(4-dimethylaminophenyl)-methyl]benzamide

Product 1

HCID 30880452-(2-Diethylaminoethyl)-3-(4-dimethylaminophenyl)isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of 0.32 g of Compound A and 1.41 g of Compound B in 10 ml of N,N-diethylethylenediamine was added 0.15 g of anhydrous zinc chloride. After heating at reflux for 2.5 hours in a nitrogen gas atmosphere, the mixture was concentrated under reduced pressure. To the residue were added 15 ml of methylene chloride and 50 ml of water, and pH of the mixture was adjusted to 1 with 4N-hydrochloric acid. After shaking, the organic layer was discarded and 30 ml of methylene chloride was added to the aqueous layer. The pH was adjusted to 12 with 10N-sodium hydroxide solution. After shaking, the aqueous layer was discarded and the organic layer was washed with saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent, ethyl acetate:hexane:triethylamine=10:20:1). A major fraction was concentrated under reduced pressure to give 1.13 g of 2-(2-diethylaminoethyl)-3-(4-dimethylaminophenyl)isoindolin-1-one (Compound 18).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2.5 hours in a nitrogen gas atmosphere
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue were added 15 ml of methylene chloride and 50 ml of water, and pH of the mixture
  5. addition30 ml of methylene chloride was added to the aqueous layer
  6. stirringAfter shaking
  7. washthe organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. washThe residue was subjected to silica gel column chromatography (eluting solvent, ethyl acetate:hexane:triethylamine=10:20:1)
  11. concentrationA major fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea3b609a3e6c4a7f8b5992c62fbe6a76
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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