p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

HRID 130441

Reaction equation

HRID 130441 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.CN1CCOCC1.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>ClCCl>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:16][CH3:17])(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 590070635-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)aniline

Product 1

HCID 444527764-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (1.20 g, 5.1 mmol) in dichloromethane (35 ml) was treated with morpholinomethyl-polystyrene HL resin (2.45 g, 4.2 mmol/g loading, 10.29 mmol) followed by 4-bromobenzenesulfonyl chloride (2.60 g, 10.2 mmol). The resulting solution was stirred at room temperature overnight (˜24hours)and then the resin filtered off with methanol and the solvent evaporated in vacuo. The residue was passed through an SCX column eluting first with methanol followed by 2M ammonia in methanol. The relevant fractions were collected, combined and the solvent evaporated in vacuo. The crude product was purified by Flashmaster causing an elution gradient of 0 to 10% methanol in dichloromethane. The relevant fractions were collected, combined and the solvent evaporated to afford the title compound (E106). MS (ES+) m/e 454/456 [M+H]+.

Workup

  1. filtrationthe resin filtered off with methanol
  2. customthe solvent evaporated in vacuo
  3. washeluting first with methanol
  4. customThe relevant fractions were collected
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by Flashmaster
  7. customThe relevant fractions were collected
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-5f4f9e09ca37412db2a3eae206990843
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Linked notes

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