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

HRID 1107945Notes

Reaction equation

HRID 1107945 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].I[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CCOC(C)=O>CN(C=O)C>[CH2:24]([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)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 123801-IodooctaneHCID 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-dimethylpropanamide (700 mg) was dissolved in DMF (7 ml) and Na (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-623113e96ce14d7f98c3456710d12af0
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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