SYNTHESIS OF DERIVATIVES OF 1-ARYL-1,2,3,4-TETRAHYDROISOQUINOLINES
Abstract
1-Aryltetrahydroisoquinoline derivatives (1–11) were dissolved in ethanol in a round-bottom flask. To the resulting solution, equimolar amounts of 3-chloromethyl-4-(methoxy)benzaldehyde (12) and potassium carbonate were added sequentially. The reaction mixture was stirred under reflux at the boiling temperature of ethanol for 4–6 hours using a magnetic stirrer. The progress of the reaction and the purity of the obtained compounds were monitored by thin-layer chromatography (TLC) on Silufol L/W 10Ч20 cm, 254 nm plates. A chloroform:methanol (16:1) solvent system was used for chromatography. Spots were visualized using an iodine chamber and Dragendorff’s reagent. After completion of the reaction, the solvent was removed under reduced pressure. The residue was extracted with chloroform and dried over anhydrous sodium sulfate. The obtained products (13–23) were recrystallized from acetone. The structures of the synthesized compounds were confirmed and established using IR, mass spectrometry, HPLC (RTT), and NMR spectroscopy.
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