Chloroform → 4-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

HRID 1788990Notes

Reaction equation

HRID 1788990 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19](CC3C=CC=CC=3)[CH2:18][CH2:17]2)[CH:3]=1.C(Cl)(Cl)Cl>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[CH:3]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 133599914-Amino-6,7-dimethoxy-2-(4-benzylpiperazin-1-yl)quinoline

Product 1

HCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinolineYield 51.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Amino-6,7-dimethoxy-2-(4-benzylpiperazin-1-yl)quinoline (6.2 g) in ethanol (300 ml) with 5% Pd/C catalyst was stirred at 50° under an atmosphere of hydrogen (50 p.s.i.) for 20 hours. The mixture was cooled, chloroform (100 ml) added and the solution filtered through "Solkafloc". The solid was washed with chloroform-methanol (1:1, 4×100 ml) and the combined filtrates evaporated in vacuo. The residue was partitioned between chloroform-sodium carbonate solution (10%), the organic layer removed, the aqueous phase saturated with salt and further extracted with chloroform. The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to yield 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (2.42 g). Spectroscopy showed this product to be the same as that of Example 32.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe solution filtered through "Solkafloc"
  3. washThe solid was washed with chloroform-methanol (1:1, 4×100 ml)
  4. customthe combined filtrates evaporated in vacuo
  5. customThe residue was partitioned between chloroform-sodium carbonate solution (10%)
  6. customthe organic layer removed
  7. extractionthe aqueous phase saturated with salt and further extracted with chloroform
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0355ae516294cdf811e5110b87ff144
Source dataset
uspto-grants-1987_08
Patent number
US04686228

Reaction notes

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