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

HRID 273506Notes

Reaction equation

HRID 273506 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-piperizine (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-52bcacf0c2de49e48f2df3831b6568a6
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

Loading…