Water → 1-(3-Methoxy-4-nitrophenyl)piperazine

HRID 419637Notes

Reaction equation

HRID 419637 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6](C)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].CS([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazineHCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene

Product 1

HCID 39674091-(3-Methoxy-4-nitrophenyl)piperazineYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene (Example 113, step B) (0.5 g, 2.7 mmol) in 25 mL of DMSO was added, 1-(methylsulfonyl)piperazine (0.53 g, 3.24 mmol), and K2CO3 (1.12 g, 8.1 mmol). The mixture was heated to 130° C. for 24 h. The mixture was poured into 500 mL of H2O, filter, washed with H2O, air dried for 15 min, dissolved in DCM, dried (MgSO4), filtered, and rotovaped down to give the title compound of step A (0.87 g, 2.64 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.77 (s, 1H), 6.76 (s, 1H), 3.89 (s, 3H), 3.23-3.28 (m, 4H), 3.06-3.11 (m, 4H), 2.93 (s, 3H), 2.20 (s, 3H).

Workup

  1. filtrationfilter
  2. washwashed with H2O, air
  3. customdried for 15 min
  4. dissolutiondissolved in DCM
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e24899715f114682b6d15d7ceb88ce50
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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