Piperazine → HCID 23513735, compound

HRID 353462Notes

Reaction equation

HRID 353462 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[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][CH:15]=[C:16]([Cl:19])[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 23513728HCID 23513728, compound

Product 1

HCID 23513735HCID 23513735, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The requisite 1-(1-benzenesulphonyl-6-chloroindol-2-ylsulphonyl)piperazine starting material was prepared as follows. A solution of 1-benzene sulphonyl-6-chloroindol-2-ylsulphonyl chloride (5.0 g, 12.8 mmol) in dichloromethane (50 ml) was added dropwise to a stirred solution of piperazine (6.62 g, 6 eq.) in dichloromethane (100 ml), and the mixture stirred for a further 4 hrs. giving a yellow solution. This was then evaporated and dried overnight under high vacuum. The residue was purified by flash chromatography using Merck silica (Art. 9385), eluting with dichloromethane containing methanol (06%), to give 1-(1-benzenesulphonyl-6-chloroindol-2-ylsulphonyl)piperazine as an off-white solid (3.68 g, 68% yield); 1H NMR (CDCl3) 2.75 ppm (m, 4H), 3.3 ppm (m, 4H), 7.45 ppm (d, 1H), 7.6 ppm (m, 3H), 7.7 ppm (m, 1H), 7.75 ppm (d, 1H), 8.0 ppm (d, 2H), 8.15 ppm (s, 1H); MS (M+H)+ 440/442.

Workup

  1. customThe requisite 1-(1-benzenesulphonyl-6-chloroindol-2-ylsulphonyl)piperazine starting material was prepared
  2. customgiving a yellow solution
  3. customThis was then evaporated
  4. customdried overnight under high vacuum
  5. customThe residue was purified by flash chromatography
  6. washeluting with dichloromethane
  7. additioncontaining methanol (06%)

Sources & evidence

ORD record
ord-d8c8861360c740389ca9e76a96b48f11
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Reaction notes

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