4-Quinolinecarboxaldehyde → 2-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine

Beteiligte Stoffe

Reaktionsschritte

1,2,3,4-tetrahydro-5-aminoisoquinoline (500 mg, 3.37 mmol) was dissolved in tetrahydrofuran (15 mL) then added 4-quinolinecarboxaldehyde (556 mg, 3.54 mmol) and sodium triacetoxyborohydride (786 mg, 3.71 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate then concentrated under vacuum. The remaining residue was dissolved in ethyl acetate then washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude material was purified by silica gel chromatography (50% to 80% ethyl acetate/hexane) to afford 2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine (805 mg) as a yellow solid. MS (ESI, pos. ion) m/z: 290.1 (M+1).

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