Triethylamine → 1-[(6-Chlorobenzo[b]thiophen-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine

HRID 352826Notes

Reaction equation

HRID 352826 reaction equation
Cl.[CH3:2][CH:3]([CH3:11])[CH2:4][CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([S:21](Cl)(=[O:23])=[O:22])[S:18][C:17]=2[CH:25]=1.C(N(CC)CC)C>O.C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([S:21]([N:9]3[CH2:8][CH2:7][NH:6][CH:5]([CH2:4][CH:3]([CH3:11])[CH3:2])[CH2:10]3)(=[O:23])=[O:22])[S:18][C:17]=2[CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 227109842-(2-Methylpropyl)piperazine Hydrochloride

Product 1

HCID 227099811-[(6-Chlorobenzo[b]thiophen-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a methylene chloride solution (30 ml) of 2-(2-methylpropyl)piperazine hydrochloride (353 mg) were added 6-chlorobenzo[b]thiophene-2-sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 3 hours. Distilled water and methylene chloride were added. The water layer thus obtained was extracted three times with methylene chloride. 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=1:100), whereby the title compound (363 mg) was obtained as a pale yellow oil.

Workup

  1. extractionwas extracted three times with methylene chloride
  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-0e28ca56636e46a886299124ec652c3e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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