Piperazine → 2-Methyl-4-(piperazin-1-yl)quinoline

HRID 333947

반응식

HRID 333947 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(OCCO)C>[CH3:12][C:4]1[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 779734-Chloro-2-methylquinoline

생성물 1

HCID 7023182-Methyl-4-(piperazin-1-yl)quinoline수율 85%

시약·촉매·용매 1

HCID 8076Glycol monoethyl ether용매

반응 조건

온도
140 °C

실험 절차

4-Chloro-2-methylquinoline (1.8 g, 10 mmol) and anhydrous piperazine (5.25 g, 60 mmol) were dissolved in ethyleneglycol monoethylether (15 ml) and stirred at 140° C. overnight. The mixture was concentrated under reduced pressure, toluene was added (2×100 ml) and the solvent removed under reduced pressure. To the residue was added 0.5 M NaOH (100 ml) and the mixture was extracted with a mixture of dichloromethane/diethylether/ethyl acetate (1:1:1, 3×100 ml). The combined organic phases were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. 2.78 g of an off-white solid (8.5 mmol, 85%) were obtained that were used directly in the next step.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure, toluene
  2. additionwas added (2×100 ml)
  3. customthe solvent removed under reduced pressure
  4. additionTo the residue was added 0.5 M NaOH (100 ml)
  5. extractionthe mixture was extracted with a mixture of dichloromethane/diethylether/ethyl acetate (1:1:1, 3×100 ml)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-c1581ae54b9d4b08ba0367fd12948db5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883791B2

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