Piperazine → 1-(1-Benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine

HRID 353459Notes

Reaction equation

HRID 353459 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[S:20](Cl)(=[O:22])=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[S:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)(=[O:22])=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride

Product 1

HCID 235137361-(1-Benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The requisite 1-(1-benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows. A solution of 1-benzenesulphonyl-5-chloroindol-2-ylsulphonyl chloride (10.0 g, 25.6 mmol) in dichloromethane (100 ml) was added dropwise to a stirred solution of piperazine (13.23 g, 6 eq.) in dichloromethane (200 ml), and the mixture stirred for a further 2 hrs. The reaction mixture was then washed with water (3×200 ml), dried (Phase-Separating paper) and evaporated to give a red oil which was purified by flash chromatography using Merck silica (Art. 9385), eluting with dichloromethane containing methanol (0-6%), to give 1-(1-benzene sulphonyl-5-chloroindol-2-ylsulphonyl)piperazine as a colourless solid, 1H NMR (CDCl3) 2.95 ppm (m, 4H), 3.4 ppm (m, 4H), 7.4 ppm (m, 4H), 7.55 ppm (m, 2H), 8.0 ppm (d, 2H), 8.0 ppm (d, 1H); MS (M+H)+ 440/442.

Workup

  1. customThe requisite 1-(1-benzenesulphonyl-5-chloroindol-2-ylsulphonyl)piperazine starting material was prepared
  2. washThe reaction mixture was then washed with water (3×200 ml)
  3. customdried
  4. custom(Phase-Separating paper)
  5. customevaporated
  6. customto give a red oil which
  7. customwas purified by flash chromatography
  8. washeluting with dichloromethane
  9. additioncontaining methanol (0-6%)

Sources & evidence

ORD record
ord-1c85d5a2fe9e48ba806e6aa1af295e3c
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Reaction notes

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