Piperazine → HCID 70199140, compound

HRID 2392573Notes

Reaction equation

HRID 2392573 reaction equation
Cl[C:2]1[C:3]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:4]=2[S:5](=[O:8])(=[O:7])[CH:6]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.ClS(Cl)(=O)=O>ClCCl>[Cl:13][C:10]1[CH:11]=[CH:12][C:3]2[C:2]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:6][S:5](=[O:8])(=[O:7])[C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 24648Sulfuryl chlorideHCID 18980222HCID 18980222, compound

Product 1

HCID 70199140HCID 70199140, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,6-dichlorobenzo[b]thiophene-1,1-dioxide (16.00 g, 0.0681 mol), piperazine (20.52 g, 0.238 mol) and dichloromethane (300 ml) was heated to reflux. After 1 hour, TLC analysis showed the dichlorosulfone (Rf =0.47, 30% ethyl acetate in hexanes, silica gel) to be consumed. The cloudy mixture was washed with 0.25 N NaOH (400 ml), H2O (300 ml), brine (250 ml), dried (Na2SO4), and the solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 50% methanol in dichloromethane, to afford 12.90 g (66.5%) of a yellow solid. A 1.60 g sample was recrystallized from dichloromethane/ether yielding 0.480 g of light yellow crystals: m.p. 154° C. dec.

Workup

  1. temperaturewas heated to reflux
  2. customto be consumed
  3. washThe cloudy mixture was washed with 0.25 N NaOH (400 ml), H2O (300 ml), brine (250 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 50% methanol in dichloromethane

Sources & evidence

ORD record
ord-81814a850ae4493a935a7ca92b103bf2
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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