Potassium Carbonate → 1-Methyl-4-(3-methyl-4-nitrophenyl)piperazine

HRID 1406415Notes

Reaction equation

HRID 1406415 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 184397471-Methyl-4-(3-methyl-4-nitrophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-fluoro-2-nitrotoluene (2.5 g, 16 mmol), N-methylpiperazine (2 mL, 18 mmol) and potassium carbonate (2.7 g, 19 mmol) in DMSO (7 mL) was stirred and heated at 100° C. for 2 hours. The reaction mixture was cooled to ambient temperature and then diluted with ethyl acetate (100 mL), washed with water (3×30 mL), brine, dried (MgSO4) and concentrated in vacuo. The resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane—40% methanol/dichloromethane (gradient) to afford the desired title compound as a yellow solid, 3.67 g, 97%.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with water (3×30 mL), brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product was purified by flash chromatography on SiO2 eluting with dichloromethane—40% methanol/dichloromethane (gradient)

Sources & evidence

ORD record
ord-1d672d88ecbf4736a2de59c410b2895e
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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