Hydrochloric Acid → 3-(2-Aminophenyl)-2-[2-(diethylamino)ethyl]-2,3-dihydro-1H-isoindol-1-one--hydrogen chloride (1/2)

HRID 231854Notes

Reaction equation

HRID 231854 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH2:5][NH:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2)[CH3:2].[ClH:25]>C(Cl)Cl>[ClH:25].[ClH:25].[NH2:10][C:9]1[CH:19]=[CH:20][CH:21]=[CH:22][C:8]=1[CH:7]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11](=[O:18])[N:6]1[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14502012HCID 14502012, compound

Product 1

HCID 30880283-(2-Aminophenyl)-2-[2-(diethylamino)ethyl]-2,3-dihydro-1H-isoindol-1-one--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 400 ml of methylene chloride was dissolved 26.7 g of 11-(2-diethylaminoethylamino)-5,11-dihydro-6H-dibenz[b,e]azepin-6-one, and dry hydrogen chloride gas was blown into the solution with stirring. The reaction solution was concentrated under reduced pressure and 100 ml of acetonitrile was added to the residue. The mixture was heated at reflux for an hour. After allowing the mixture to stand at room temperature, precipitated crystals were separated by filtration to give 28.02 g of 3-(2-aminophenyl)-2-(2-diethylaminoethyl)isoindolin-1-one dihydrochloride 0.25 hydrate (Compound 1').

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and 100 ml of acetonitrile
  2. additionwas added to the residue
  3. temperatureThe mixture was heated
  4. temperatureat reflux for an hour
  5. customto stand at room temperature
  6. customprecipitated crystals
  7. customwere separated by filtration

Sources & evidence

ORD record
ord-c2297445814748de8eddc68179e8e23e
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

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