2-(1-Piperazinylmethyl)quinoline → HCID 15487637, compound

HRID 365306Notes

Reaction equation

HRID 365306 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2([CH3:16])[CH3:15].[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(Cl)(Cl)Cl>[CH3:15][C:8]1([CH3:16])[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([O:4][CH2:3][CH2:2][N:31]3[CH2:32][CH2:33][N:28]([CH2:27][C:18]4[CH:19]=[CH:20][C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:17]=4)[CH2:29][CH2:30]3)[CH:6]=2)[NH:10][C:9]1=[O:14]

Participants

4

Reactant 2

HCID 43753132-(1-Piperazinylmethyl)quinolineHCID 130846875-(2-Chloroethoxy)-1,3-dihydro-3,3-dimethyl-2H-indol-2-one

Product 1

HCID 15487637HCID 15487637, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

5-(2-Chloroethoxy)-3,3-dimethyl-2,3-dihydroindol-2-one (182 mg, 3.0 mmol) and N--(2-quinolylmethyl)piperazine (690 mg, 3.0 mmol) were mixed, followed by stirring at 150° C. for 3 hours under an argon gas stream. The resulting mixture was allowed to cool down, and was then dissolved in chloroform. The thus-obtained solution was washed with water and then dried over anhydrous sodium sulfate. After the solution was concentrated under reduced pressure, the residue was purified by chromatography on a silica gel column while using chloroform-methanol (10:1) as an eluent. Fractions containing the target compound were collected and then concentrated under reduced pressure. The concentrate was crystallized from n-hexane and was then recrystallized from ethyl acetate-ethyl ether, whereby 240 mg of the title compound were obtained as pale yellow powder (yield: 73%).

Workup

  1. temperatureto cool down
  2. washThe thus-obtained solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter the solution was concentrated under reduced pressure
  5. customthe residue was purified by chromatography on a silica gel column
  6. additionFractions containing the target compound
  7. customwere collected
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was crystallized from n-hexane
  10. customwas then recrystallized from ethyl acetate-ethyl ether

Sources & evidence

ORD record
ord-76bf6ae4bfc84ee9875c60f7aa491d23
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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