Acetamide, N-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]- → 4-(4-Methylpiperazine-1-sulfonyl)aniline

HRID 916564Notes

Reaction equation

HRID 916564 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1>Cl.O1CCOCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 764494Acetamide, N-[4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-

Product 1

HCID 5672614-(4-Methylpiperazine-1-sulfonyl)anilineYield 53%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

N-[4-(4-methylpiperazine-1-sulfonyl)phenyl]acetamide (2 g, 6.7 mmol) was dissolved in 3 N HCl (50 mL) and 1,4-dioxane (12 mL). The reaction mixture was refluxed for 1 h, evaporated under vacuum, and the resulting mixture made basic with 30% NH4OH. The desired product was extracted with CH2Cl2, dried (Na2SO4), filtered, and evaporated under reduced pressure to obtain 4-(4-methylpiperazin-1-sulfonyl)aniline as a white solid. MP: 210° C.; Yield 53%; 1H NMR (DMSO d6): δ 2.22 (s, 3H), 2.50 (m, 4H), 2.82 (m, 4H), 6.10 (bs, 2H), 6.62-6.67 (d, 2H, J=10 Hz), 7.32-7.36 (d, 2H, J=8 Hz).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customevaporated under vacuum
  3. extractionThe desired product was extracted with CH2Cl2
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-24cf2872f3954b1799d0478a029a05f4
Source dataset
uspto-grants-2007_09
Patent number
US07271171B2

Reaction notes

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