Pyridine → N-(2-Isopropylphenyl)-4-methoxy-3-piperazin-1-yl-benzenesulfonamide hydrochloride

HRID 429148Notes

Reaction equation

HRID 429148 reaction equation
N1C=CC=CC=1.[CH:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])([CH3:9])[CH3:8].[Cl:17]C(Cl)(Cl)C([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([S:35](Cl)(=[O:37])=[O:36])[CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[CH2:23][CH2:22]1)=O>ClCCl>[ClH:17].[CH:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][S:35]([C:29]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([N:24]2[CH2:25][CH2:26][NH:21][CH2:22][CH2:23]2)[CH:28]=1)(=[O:36])=[O:37])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 125612-IsopropylanilineHCID 11178065HCID 11178065, compound

Product 1

HCID 18354534N-(2-Isopropylphenyl)-4-methoxy-3-piperazin-1-yl-benzenesulfonamide hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.28 ml) was added to a stirred solution of 2-isopropylaniline (98 mg) and 3-(4-trichloroacetylpiperazin-1-yl)-4-methoxybenzenesulfonyl chloride (D4) (300 mg) in dichloromethane (4 ml) at room temperature. After 18 h the solution was washed with 1M hydrochloric acid (5 ml) then water (5 ml). The organic phase was stirred vigourously with 20% aq. potassium hydroxide (0.5 ml) for 18 h. A 10% aqueous solution of KH2PO4 (8 ml) was then added to the mixture and after 0.25 h stirring the layers were separated. The organic layer was dried (Na2SO4), acidified with 1M ethereal hydrogen chloride (2 ml) and concentrated to an oil which was stirred with acetone/diethyl ether to afford the title compound (E79) as a white solid (0.224 g, 83%). MH+ 390.

Workup

  1. washAfter 18 h the solution was washed with 1M hydrochloric acid (5 ml)
  2. additionA 10% aqueous solution of KH2PO4 (8 ml) was then added to the mixture and after 0.25 h
  3. stirringstirring the layers
  4. customwere separated
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated to an oil which
  7. stirringwas stirred with acetone/diethyl ether

Sources & evidence

ORD record
ord-b90517812add4050ac54573df420bbe4
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Reaction notes

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