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

HRID 238196Notes

Reaction equation

HRID 238196 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O1CCOCC1>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([S:28]([C:25]2[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 166655764-(4-BOC-piperazinosulfonyl)bromobenzeneYield 91.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 1-piperazine-carboxylate (932 mg, 5 mmol) and triethyl amine (836 μL, 6 mmol) in dioxane (10 mL) was added 4-bromo-benzenesulfonyl chloride (1.28 g, 5 mmol). A white precipitate begins to form almost immediately. The reaction mixture was stirred for 1 hour at room temperature and the filtered. The filtrate was concentrated in vacuo to yield the product as a shiny white solid (1.85 g, 91%). 1H NMR (CDCl3) δ 1.44 (s, 9H), 3.01 (t, 4H, J=5.1 Hz), 3.53 (t, 4H, J=5.1 Hz), 7.64 (dt, 2H, J=2.1, 8.7 Hz), 7.70 (dt, 2H, J=2.1, 8.7).

Workup

  1. customto form almost immediately
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6797a39b7a984d2395102b2fa1f3c1ee
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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