p-Bromobenzenesulfonyl chloride → 4-(4-BOC-piperazinosulfonyl)bromobenzene

HRID 352824Notes

Reaction equation

HRID 352824 reaction equation
C(N(C(C)C)CC)(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:31]2[CH2:30][CH2:29][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:33][CH2:32]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 166655764-(4-BOC-piperazinosulfonyl)bromobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (4.00 ml) was added to a solution of 4-bromobenzenesulfonyl chloride (3.00 g) and 1-(tert-butoxycarbonyl)piperazine (2.40 g) in methylene chloride (50 ml) at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1→1:1), followed by reprecipitation in a hexane—methylene chloride system, whereby the title compound (4.47 g) was obtained as a colorless solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1→1:1)
  4. customfollowed by reprecipitation in a hexane—methylene chloride system, whereby the title compound (4.47 g)
  5. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-7d223fde63e14ff6a8cb3d0441f8c8d8
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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