4-(4-BOC-piperazinosulfonyl)bromobenzene → 1-(4-Bromobenzene-1-sulfonyl)piperazine

HRID 238197Notes

Reaction equation

HRID 238197 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([S:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 166655764-(4-BOC-piperazinosulfonyl)bromobenzene

Product 1

HCID 7129241-(4-Bromobenzene-1-sulfonyl)piperazineYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-Bromo-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 1.23 mmol) was dissolved in a mixture of dichloromethane (5 mL) and trifluoroacetic acid (5 mL) and stirred at room temperature overnight. The reaction mixture was then concentrated in vacuo and then dissolved in dichloromethane and washed with saturated sodium bicarbonate solution and then water. The organic layer was then dried over magnesium sulfate and concentrated in vacuo to yield the product as a white solid (329 mg, 88%). 1H NMR (CDCl3) δ 1.77 (s, 1H), 2.96 (m, 4H), 3.01 (m, 4H), 7.64 (dt, 2H, J=2.1, 8.7 Hz), 7.69 (dt, 2H, J=2.1, 8.7 Hz).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutiondissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-385791ade7814adf8f92beba876e566b
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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