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Potassium Carbonate → HCID 67465008, 화합물

HRID 1522838
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HRID 1522838 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[N:8][CH:7]=[CH:6]2.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[N:8][CH:7]=[CH:6]2
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 178487746HCID 178487746, 화합물

생성물 1

HCID 67465008HCID 67465008, 화합물수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 6-methoxyisoquinoline-1-ol (1.00 g, 5.71 mmol) in acetone, K2CO3 (4.73 g, 34.26 mmol) and N-chloroethyl-piperidine hydrochloride salt (1.37 g, 7.42 mmol) were added. The solution was heated to reflux for 6 hours. The solution was evaporated to dryness. The residue was hydrolyzed by adding water, then extracted with ethyl acetate. The organic layers were separated and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica-gel; methylene chloride/methanol=9/1 v/v) to give a yellow oil product, 1.50 g, 92.0% yield. MS: 287.2 [M+H]+. 1H NMR (DMSO-d6, 300 MHz) δ 8.11 (d, 1H, J=9.0 Hz), 7.39 (d, 1H, J=7.5 Hz), 7.10-7.13 (m, 2H), 6.51 (d, 1H, J=7.5 Hz), 4.02 (t, 2H, J=6.6 Hz), 3.86 (s, 3H), 2.55 (t, 2H, J=6.5 Hz), 2.41 (br, 4H), 1.52-1.44 (m, 4H), 1.37-114 (m, 2H).

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 6 hours
  3. customThe solution was evaporated to dryness
  4. additionby adding water
  5. extractionextracted with ethyl acetate
  6. customThe organic layers were separated
  7. dry with materialdried over anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by flash chromatography (silica-gel; methylene chloride/methanol=9/1 v/v)
  10. customto give a yellow oil product, 1.50 g, 92.0% yield

출처 및 근거

ORD 기록
ord-0040c1ca9baf4b7bbb608ef5631cf000
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09078888B2

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