Sodium Bicarbonate → 1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-nitrophenyl)ethanone

HRID 850515

Reaktionsgleichung

Reaktionsgleichung von HRID 850515
[CH3:1][O:2][C:3]1[C:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O-])=[O:30])=[CH:24][CH:23]=1)([O-:21])=[O:20].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:29](=[O:30])[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:27][CH:26]=1)[CH2:7][CH2:6]2

Komponenten

8

Edukt 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6931101(4-Nitrophenyl)acetateHCID 193633206-Methoxy-5-pentyloxy-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 193633041-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-nitrophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Methoxy-5-pentyloxy-1,2,3,4-tetrahydroisoquinoline (116 mg, 0.465 mmol), (4-nitrophenyl)acetate (101.1 mg, 0.558 mmol) and 1-hydroxybenzotriazol hydrate (81.7 mg, 0.605 mmol) were dissolved in DMF (2 ml), and WSC hydrochloride (125 mg, 0.651 mmol) was added to this solution under ice-cooling. After stirring at room temperature for 3 hours, ethyl acetate (3 ml) and saturated aqueous sodium hydrogencarbonate solution (3 ml) were added to the reaction mixture to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure to give a crude product of 1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-nitrophenyl)ethanone. This product was used for the next reaction.

Aufarbeitung

  1. temperaturecooling
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-da005e14829e466da540592819bcca09
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017919

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