Piperazine → HCID 10430452, compound

HRID 549263Notes

Reaction equation

HRID 549263 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[Cl:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[ClH:20].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 67157027HCID 67157027, compound

Product 1

HCID 10430452HCID 10430452, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-benzenesulfonyl-4-chloro-quinoline (35 mg, 0.11 mmol) and piperazine (0.5 g, 2.5 mmol) in acetonitrile (2 mL) was heated at 80° C. over night. The mixture was extracted with toluene and water. The organic phase was purified by chromatography on silica gel eluted with CHCl3 saturated with NH3 (gas). The pure product was dissolved in ethyl acetate and HCl (gas) in diethyl ether was added. The resulting oily residue was dissolved in methanol and ethyl acetate and evaporated to yield a white solid (24 mg, 77%). MS m/z: 354 [M+H+]. 1H NMR (270 MHz, CH3OH-D4) δ ppm 3.52 (m, 4H) 4.13 (m, 4H) 7.36 (d, J=7.18 Hz, 1H) 7.57 (m, 3H) 8.01 (m, J=12.25, 8.54 Hz, 3H) 8.28 (d, J=8.91 Hz, 1H) 8.63 (d, J=6.68 Hz, 1H) 8.69 (s, 1H).

Workup

  1. extractionThe mixture was extracted with toluene and water
  2. customThe organic phase was purified by chromatography on silica gel
  3. washeluted with CHCl3 saturated with NH3 (gas)
  4. dissolutionThe pure product was dissolved in ethyl acetate
  5. additionHCl (gas) in diethyl ether was added
  6. dissolutionThe resulting oily residue was dissolved in methanol
  7. customethyl acetate and evaporated

Sources & evidence

ORD record
ord-80cc813afeb8457394908cb899ce444d
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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