N-methyl-2-pyrrolidone → HCID 66643060, compound

HRID 869258Notes

Reaction equation

HRID 869258 reaction equation
CS(O[CH2:6][CH2:7][N:8]([CH3:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)(=O)=O.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CN1C(=O)CCC1>O>[CH3:18][N:8]([CH2:7][CH2:6][N:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 531671-MethylpiperazineHCID 86662056HCID 86662056, compound

Product 1

HCID 66643060HCID 66643060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[methyl(3-nitrophenyl)amino]ethyl methanesulfonate (Preparation Example 472) (1.0 g), 1-methylpiperazine (1.61 mL) and NMP (5 mL) was reacted at 130° C. for 30 minutes using a microwave reaction system. The reaction liquid was diluted with water, extracted with a mixed solvent of chloroform and methanol (10:1), and then washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=10:1:0.1) to give N-methyl-N-[2-(4-methylpiperazin-1-yl)ethyl]-3-nitroaniline (890 mg) as a yellow oil.

Workup

  1. customwas reacted at 130° C. for 30 minutes
  2. customa microwave reaction system
  3. customThe reaction liquid
  4. extractionextracted with a mixed solvent of chloroform and methanol (10:1)
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=10:1:0.1)

Sources & evidence

ORD record
ord-cc96f34ab50d4849a1be0180a50338a8
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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