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

HRID 1293640Notes

Reaction equation

HRID 1293640 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 (22ml) was added drop wise. The reaction mixture was stirred at room temperature for 16h 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-138cebf3c80747c48e82f0511e7a76f6
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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