Chlorosuccinimide → 4-[2-(Dipropylamino)ethyl]indol-2-one

HRID 1766628Notes

Reaction equation

HRID 1766628 reaction equation
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=O.[CH2:9]([N:12]([CH2:24][CH2:25][CH3:26])[CH2:13][CH2:14][C:15]1C=CC=C2[C:16]=1[CH:17]=[CH:18]N2)[CH2:10][CH3:11]>C1(C)C=CC=CC=1>[CH2:24]([N:12]([CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14][C:15]1[C:4]2[C:3]([CH:18]=[CH:17][CH:16]=1)=[N:2][C:6](=[O:7])[CH:5]=2)[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 30860544-(2-di-N-propylaminoethyl)indole

Product 1

HCID 211117034-[2-(Dipropylamino)ethyl]indol-2-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-chlorosuccinimide (2.52 g, 18.9 mmol) was added to a solution of 4-[2-(dipropylamino)ethyl]indole (IV) (3 g, 12.28 mmol) in toluene (10 mL) and was stirred at room temperature for 1 h. The resultant mixture was washed with an aqueous solution of NaOH 5% and then an aqueous solution of HCl 1N (30 mL) was added to the organic layer and was heated at reflux temperature for 1 h. When the mixture reached room temperature, the organic layer was separated and the aqueous layer was basified with an aqueous solution of NaOH and extracted with AcOEt. The organic layer was dried, filtered and concentrated to obtain 2.1 g (66%) of 4-[2-(dipropylamino)ethyl]indol-2-one (I), which was purified and converted into its hydrochloride salt.

Workup

  1. washThe resultant mixture was washed with an aqueous solution of NaOH 5%
  2. additionan aqueous solution of HCl 1N (30 mL) was added to the organic layer
  3. temperaturewas heated
  4. temperatureat reflux temperature for 1 h
  5. customreached room temperature
  6. customthe organic layer was separated
  7. extractionextracted with AcOEt
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-75d8e5b705d24ac4b7b7cf1e1bafe3a8
Source dataset
uspto-grants-2007_06
Patent number
US07230118B2

Reaction notes

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