p-Bromobenzenesulfonyl chloride → HCID 1274681, compound

HRID 1852432Notes

Reaction equation

HRID 1852432 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:12]([CH:19]1[CH2:24][CH2:23][N:22]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chloride2×HCID 317384-BenzylpiperidineHCID 81531Diisopropylethylamine

Product 1

HCID 1274681HCID 1274681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-Bromobenzene-1-sulfonyl chloride (100 mg, 0.391 mmol) dissolved in DCM (2.0 mL) at ambient temperature. 4-Benzylpiperidine (89 mg, 0.51 mmol) were diluted in DCM (2.0 mL) and treated with DIPEA (0.205 mL, 1.174 mmol) at ambient temperature. To this mixture a solution of 4-bromobenzene-1-sulfonyl chloride (100 mg, 0.391 mmol) dissolved in DCM (2.0 mL) was added and the reaction stirred at ambient temperature for 17 hours. The reaction was then concentrated in vacuo to afford the title compound, which was used without further purification. LRMS (ESI) calc'd for C18H20BrNO2S [M+H}+: 394. found 394

Workup

  1. additionwas added
  2. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-9560e107558a4f7f9231fea983ebb313
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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