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

HRID 850515

Reaction equation

HRID 850515 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-da005e14829e466da540592819bcca09
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Linked notes

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