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

HRID 130429Notes

Reaction equation

HRID 130429 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][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl.N1C=CC=CC=1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([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][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 590070925-(cis-3,5-Dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]aniline

Product 1

HCID 590071064-Bromo-N-{5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]phenyl}benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-[(phenylmethyl)oxy]aniline (D39) (500 mg, 1.61 mmol) in dichloromethane (8 ml) and pyridine (8 ml) was added 4-bromobenzenesulfonyl chloride (820 mg, 3.21 mmol) and the resulting mixture stirred at room temperature, under an atmosphere of argon for 2 hours. The mixture was then reduced in vacuo, azeotroped with methanol and the residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium hydrogen carbonate (75 ml). The layers were separated, the aqueous re-extracted with dichloromethane (50 ml) and the combined organic layers washed with brine (125 ml), dried over anhydrous magnesium sulphate, filtered and reduced in vacuo. The residue was purified by chromatography on silica gel (gradient: dichloromethane:methanol 25:1 to 10:1) to afford the title compound (D40). MS (ES+) m/e 530/532 [M+H]+.

Workup

  1. customazeotroped with methanol
  2. customthe residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium hydrogen carbonate (75 ml)
  3. customThe layers were separated
  4. extractionthe aqueous re-extracted with dichloromethane (50 ml)
  5. washthe combined organic layers washed with brine (125 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customThe residue was purified by chromatography on silica gel (gradient: dichloromethane:methanol 25:1 to 10:1)

Sources & evidence

ORD record
ord-5b32ccca332a45c1b8c721c82cbaace7
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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