Hydrochloric Acid → 2-Methyl-5-(2-piperazin-1-ylethoxy)quinoline

HRID 1295568노트

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HRID 1295568 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[N:3]=1.Cl.C(OCC)C>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11394642tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate

생성물 1

HCID 112542672-Methyl-5-(2-piperazin-1-ylethoxy)quinoline수율 91%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
40 °C

실험 절차

tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate (1.04 g, 2.8 mmol) was dissolved in ethanol (60 mL) and treated with 1 M hydrochloric acid in diethyl ether (16 mL, 16 mmol) and stirred at 40° C. for 17 h. The reaction mixture was filtered and the white solid was collected and dried in vacuo. The hydrochloride salt precipitate was dissolved in water (25 mL) and potassium carbonate was added until the pH reached 10. The aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL) then 10% methanol in dichloromethane (4×100 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo, affording the title compound as a brown oil (0.69 g, 91%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe white solid was collected
  3. customdried in vacuo
  4. dissolutionThe hydrochloride salt precipitate was dissolved in water (25 mL)
  5. additionpotassium carbonate was added until the pH
  6. washThe aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2f53d0bbd9f543a299506b8d11dd627e
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244726B2

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