Potassium Carbonate → N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamide

HRID 1890137

반응식

HRID 1890137 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[OH:28])[CH2:7][CH2:6]2.Cl[CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])[CH2:7][CH2:6]2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 16738306N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide

생성물 1

HCID 68008900N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-(2-hydroxyethoxy)ethoxy)-5-methylbenzamide수율 52.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The mixture of 4a (0.65 g, 1.6 mmol), 2-(2-chloroethoxy)ethanol (0.64 g, 5.1 mmol), potassium carbonate (0.71 g, 5.1 mmol) in of N,N-Dimethylformamide (DMF) (25 mL) was refluxed over night under an atmosphere of nitrogrn. The reaction mixture was cooled to room temperature and quenched with 100 mL water. The aqueous solution was extracted with ethyl acetate (3 X2 50 mL). The combined organic layer was washed with brine (3×30 mL) and dried over Na2SO4. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90, v/v) as the mobile phase to afford compound 5a (0.41 g; 51% yield) as a viscous yellow oil. 1H NMR (300 MHz, CDCl3): 1.68-1.79 (m, 4H), 2.31 (s, 3H), 2.50-2.60 (m, 2H), 2.72-2.76 (m, 2H), 2.82-2.85 (m, 2H), 3.46-3.60 (m, 8H), 3.80-3.90 (m, 8H), 4.18-4.24 (m, 2H), 6.49 (s, 1H), 6.58 (s, 1H), 6.79-6.83 (d, 1H), 7.16-7.24 (m, 1H), 7.98-7.80 (m, 1H), 8.18-8.26 (s, 1H).

후처리

  1. temperaturewas refluxed over night under an atmosphere of nitrogrn
  2. customquenched with 100 mL water
  3. extractionThe aqueous solution was extracted with ethyl acetate (3 X2 50 mL)
  4. washThe combined organic layer was washed with brine (3×30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue was purified by silica gel column chromatography with methanol/dichloromethane (10/90

출처 및 근거

ORD 기록
ord-15c68c1c5c5e4195b30dcf7e0b2b75d2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08506927B2

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