Sodium Carbonate → 1-[4-Chloro-3-(4-methyl-piperazine-1-sulfonyl)-phenyl]-propan-2-one

HRID 1093010Notes

Reaction equation

HRID 1093010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12]([N:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 578311052-Chloro-5-(2-oxopropyl)benzene-1-sulfonyl chloride

Product 1

HCID 665884901-[4-Chloro-3-(4-methyl-piperazine-1-sulfonyl)-phenyl]-propan-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-5-(2-oxopropyl)-benzenesulphonyl chloride (174a) (2.0 g, 7.5 mmol) is dissolved in dioxan (50 ml) with stirring. Sodium carbonate (7.5 ml, 2M solution, 2 eq.) is added followed by 1-methyl piperazine (0.75 g, 7.5 mmol). After 30 min the reaction mixture is poured onto water (250 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts are washed with water (2×100 ml) followed by brine (100 ml) and dried (MgSO4). After filtration the solvent is removed and the product is purified by chromatography on silica, eluting with ethyl acetate/hexane (1:2) to afford the titled compound.

Workup

  1. additionAfter 30 min the reaction mixture is poured onto water (250 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic extracts are washed with water (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration the solvent
  6. customis removed
  7. customthe product is purified by chromatography on silica
  8. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-518bf3f258df4c11b3c739a96139de24
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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