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

HRID 273529Notes

Reaction equation

HRID 273529 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:21]([C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

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

Product 1

HCID 166655764-(4-BOC-piperazinosulfonyl)bromobenzeneYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring, 0° C. solution of piperazine-1-carboxylic acid tert-butyl ester (1.17 g, 6.29 mmol, 1.05 equiv) and TEA (1.67 mL, 11.98 mmol, 2.0 equiv) in DCM (10 mL) was added 4-bromo-benzenesulfonyl chloride (1.53 g, 5.99 mmol, 1 equiv). The reaction was allowed to warm to ambient temperature and stir for 3 h. The reaction solvents were evaporated and the resulting solids were dried, washed with water and filtered, yielding a white powder (2.24 g, 92% yield). MS (ESI+): m/z=306.9, LC retention time: 3.17 min. Rf=0.56 (30% EtOAc/hexanes).

Workup

  1. customThe reaction solvents were evaporated
  2. customthe resulting solids were dried
  3. washwashed with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ce0b2feff8ab4fc6ade519a8285706be
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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