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

HRID 130436Notes

Reaction equation

HRID 130436 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[NH2:12])[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:12][C:11]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:9]([N:4]3[CH2:5][C@H:6]([CH3:8])[NH:7][C@H:2]([CH3:1])[CH2:3]3)[CH:10]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 590070453-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

Product 1

HCID 115615394-Bromo-N-[3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (800 mg, 3.40 mmol) in dichloromethane (50 ml) was treated with morpholinomethyl-polystyrene HL resin (1.70 g, 4.0 mmol/g loading, 6.80 mmol) followed by 4-bromobenzenesulfonyl chloride (1.30 g, 5.09 mmol). The resulting solution was stirred at room temperature overnight and was then filtered, washing with methanol, and the filtrate concentrated in vacuo. The residue was then purified using an SCX ion exchange cartridge (Varian bond-elute) eluting with methanol followed by ammonia (2M in methanol). The appropriate fractions were combined and reduced in vacuo to afford a crude product which was purified further by chromatography on silica gel eluting with (0 to 20% methanol in dichloromethane) to afford the title compound (E101). MS (ES+) m/e 454/456 [M+H]+.

Workup

  1. filtrationwas then filtered
  2. washwashing with methanol
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was then purified
  5. washan SCX ion exchange cartridge (Varian bond-elute)
  6. washeluting with methanol
  7. customto afford a crude product which
  8. customwas purified further by chromatography on silica gel eluting with (0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a70442fd2070411aba07a4f6d225a94b
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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