Methyl iodide → 2,2-Dimethyl-N-[2-(2,3-dihydro-1-methyl-1H-indol-2-yl)phenyl]propanamide

HRID 249333Notes

Reaction equation

HRID 249333 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]([CH3:28])([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19]1)=[O:10].IC>CN(C=O)C>[CH3:7][C:8]([CH3:28])([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]1[CH3:1])=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 197613982,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Product 1

HCID 197613952,2-Dimethyl-N-[2-(2,3-dihydro-1-methyl-1H-indol-2-yl)phenyl]propanamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 9.40 g K2CO3 and 10.05 g 2,2-dimethyl-N-[2-(2,3-dihydro-1H-indol-2yl)phenyl]propanamide in 125 ml DMF at 0° C., was added 3.64 ml iodomethane. The resulting mixture was stirred twenty-eight hours at room temperature. Upon dilution with water, a solid precipitated, which was collected and washed with water. Recrystallization from EtOH/water yielded 4.86 g solid, m.p. 133°-135° C.

Workup

  1. customUpon dilution with water, a solid precipitated
  2. customwhich was collected
  3. washwashed with water
  4. customRecrystallization from EtOH/water

Sources & evidence

ORD record
ord-5727d97233a44f3d84dbfa557d7bd00b
Source dataset
uspto-grants-1993_05
Patent number
US05214059

Reaction notes

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