Triethylamine → 1-(3-Bromobenzenesulfonyl)-4-methylpiperazine

HRID 449201Notes

Reaction equation

HRID 449201 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CCN(CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chlorideHCID 531671-Methylpiperazine

Product 1

HCID 294021141-(3-Bromobenzenesulfonyl)-4-methylpiperazineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-bromo-benzenesulfonyl chloride (3.914 mmol, 1.0 equiv) and 1-methyl-piperazine (7.83 mmol, 2.0 equiv) were dissolved in 15 mL DCM. Et3N (15.66 mmol, 4.0 equiv) was added via syringe to the reaction and stirred at room temperature for 2 h. The reaction was diluted with DCM, the organic phase was extracted with saturated NaHCO3 and brine and dried (Na2SO4). The organics were removed under reduced pressure to give 1-(3-bromo-benzenesulfonyl)-4-methyl-piperazine, as a white solid (1.1 g. 88% yield). 1H NMR (DMSO-d6): δ 2.14 (s, 3H), 2.35 (m, 4H), 2.92 (m, 4H), 7.62 (t, J=7.9 Hz, 2H0, 7.55 (dd, J=7.9 Hz, J=0.8 Hz, 1H), 7.85 (t, J=1.8 Hz, 1H), 7.95 (dd, J=9.1 Hz, J=0.9 Hz, 1H) MS (ES+) m/z=321 LC retention time 1.74 min.

Workup

  1. extractionthe organic phase was extracted with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. customThe organics were removed under reduced pressure

Sources & evidence

ORD record
ord-68f780d3a4494c0089c0408e986b351c
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Reaction notes

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