Triethylamine → 1-[(6-Chlorobenzo[b]thien-2-yl)sulfonyl]-3-ethylpiperazine

HRID 352801Notes

Reaction equation

HRID 352801 reaction equation
Cl.[CH2:2]([CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1)[CH3:3].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:18]=[C:17]([S:19](Cl)(=[O:21])=[O:20])[S:16][C:15]=2[CH:23]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:18]=[C:17]([S:19]([N:8]3[CH2:7][CH2:6][NH:5][CH:4]([CH2:2][CH3:3])[CH2:9]3)(=[O:21])=[O:20])[S:16][C:15]=2[CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 227107862-Ethyl piperazine hydrochloride

Product 1

HCID 227097651-[(6-Chlorobenzo[b]thien-2-yl)sulfonyl]-3-ethylpiperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a methylene chloride solution (30 ml) of 2-ethylpiperazine hydrochloride (307 mg) was added (6-chlorobenzo[b]thien-2-yl)sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 26 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (255 mg) was obtained as a pale yellow oil. MS (FAB) m/z: 345 [(M+H)+, Cl35], 347 [(M+H)+, Cl37]. 1H-NMR (CDCl3) δ: 0.95(3H,t,J=7.8 Hz), 1.24-1.46(2H,m), 2.16(1H,t,J=10.7 Hz), 2.54(1H,dt,J=2.9,11.2 Hz), 2.65-2.75(1H,m), 2.95(1H,dt,J=2.9,11.2 Hz), 3.04-3.10(1H,m), 3.65-3.72(2H,m), 7.43(1H,dd,J=8.8,2.0 Hz), 7.75(1H,s), 7.81(1H,d,J=8.8 Hz), 7.86(1H,s).

Workup

  1. extractionthe water layer was extracted three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-9c199f4918ce48d193de41e6e877a036
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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