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

Participants

Reaction Steps

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.

Provenance & Evidence