Triethylamine → 1-[(5-Bromo-2-thienyl)sulfonyl]-4-methylpiperazine

HRID 558529Notes

Reaction equation

HRID 558529 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C1COCC1>[Br:1][C:2]1[S:6][C:5]([S:7]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 6621571-[(5-Bromo-2-thienyl)sulfonyl]-4-methylpiperazineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of commercially available 5-bromo-thiophene-2-sulfonyl chloride (3.0 g, 11.5 mmol) in THF (22 ml) was added at room temperature triethylamine (1.76 ml, 12.6 mmol), the mixture was cooled (ice-water), and a solution of commercially available 1-methylpiperazine (3.82 ml, 34.4 mmol) in THF (22 ml) was added drop wise. The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (dichloromethane/methanol) and subsequent crystallization from dichloromethane/hexane to yield the title compound (3.12 g, 84%) as a white solid. MS (ISP) 324.8 [(M+H)+], mp 122° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography (dichloromethane/methanol) and subsequent crystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-25c01662f5b44b738b08b800634715f7
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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