Water → 1-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

HRID 419643Notes

Reaction equation

HRID 419643 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[CH3:13][S:14]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(=[O:16])=[O:15].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:20]2[CH2:21][CH2:22][N:17]([S:14]([CH3:13])(=[O:16])=[O:15])[CH2:18][CH2:19]2)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 598602551-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To 4-fluoro-2-(methyloxy)-1-nitrobenzene (Example 22, step A) (1 g, 5.8 mmol) in 10 mL of DMSO was added, 1-(methylsulfonyl)piperazine (1.15 g, 7.02 mmol), and K2CO3 (2.42 g, 17.5 mmol). The mixture was heated to 80° C. overnight. In the morning, the mixture was poured into 100 mL of H2O, Solid precipitated and was filtered off, washed with H2O and let air dried for a few hours. After drying under high vacuum overnight, the title compound of step A was isolated as a yellow solid. (1.09 g, 3.46 mmol, 60%). MS (ESI): 316 [M+H]+.

Workup

  1. customprecipitated
  2. filtrationwas filtered off
  3. washwashed with H2O
  4. customdried for a few hours
  5. customAfter drying under high vacuum overnight

Sources & evidence

ORD record
ord-9766c84bce6847fe88e6d47ec65005e2
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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