Ethyl Acetate → N-(1-Octyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531955Notes

Reaction equation

HRID 1531955 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:6]([CH3:22])=[C:7]2[C:11](=[C:12]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[C:13]=1[CH3:14])[NH:10][CH2:9][CH2:8]2)[CH3:3].[H-].[Na+].I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].CCOC(C)=O>CN(C=O)C>[CH2:26]([N:10]1[C:11]2[C:7](=[C:6]([CH3:22])[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[C:13]([CH3:14])[C:12]=2[NH:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:8][CH2:9]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 22247324N-(5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 15895565N-(1-Octyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamideYield 120.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(5-Dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (700 mg) was dissolved in DMF (7 ml) and NaH (P=60%, 160 mg) was added under a nitrogen atmosphere at 5° C. After stirring at the same temperature for 30 min, 1-iodooctane (240 mg) was added, which was followed by stirring at 30° C. for 3 hr. AcOEt (200 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=10/1−3/1) to give 500 mg of the title compound.

Workup

  1. stirringby stirring at 30° C. for 3 hr
  2. washthe mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAcOEt was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=10/1−3/1)

Sources & evidence

ORD record
ord-4564854d66014596afa9feacfb4d840e
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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