Methyl iodide → HCID 66642765, compound

HRID 869222Notes

Reaction equation

HRID 869222 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[NH:17][C:18](=[O:20])[CH3:19])[CH2:4][CH2:3]1.[H-].[Na+].[CH3:23]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:23][N:17]([C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2966356HCID 2966356, compound

Product 1

HCID 66642765HCID 66642765, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]acetamide (433 mg) and DMF (5 mL), 63% sodium hydride in oil (66 mg) was added under ice cooling and stirred at room temperature for 1 hour. The reaction liquid was ice cooled again, and methyl iodide (0.11 mL) was added and stirred at room temperature for 4 hours. The reaction liquid was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol) to give N-methyl-N-[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]acetamide (200 mg) as an orange solid.

Workup

  1. additionwas added under ice cooling
  2. customThe reaction liquid
  3. temperaturecooled again
  4. stirringstirred at room temperature for 4 hours
  5. customThe reaction liquid
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol)

Sources & evidence

ORD record
ord-76317e96e5714911a2ed2564452b9aec
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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