With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22990-19-8,1-Phenyl-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.
General procedure: Pd/C (254 mg, 0.12 mmol) and K3PO4*3H2O (16 mg, 0.06mmol) were placed in a Schlenk tube followed by acetonitrile(1 mL), and the resulting mixture was stirred at room temperaturefor 10 min. A solution of 1-substituted-1,2,3,4- tetrahydroisoquinoline(0.30 mmol) in acetonitrile (4 mL) was thenadded to the reaction mixture, and the Schlenk tube was carefullyand quickly vacuum purged before being filled with oxygenusing an oxygen balloon. The reaction mixture was thenstirred at 60 C until the 1-substituted-1,2,3,4- tetrahydroisoquinolinehad been completely consumed (as determined byTLC analysis). Upon completion of the reaction, the mixturewas slowly cooled to room temperature and filtered throughdiatomite to remove the Pd/C catalyst. The filtrate was thenconcentrated in vacuo to give the crude product as a residue,which was purified by flash chromatography over silica geleluting with petroleum ether and ethyl acetate to give the imineproduct 2. 1-Phenyl-3,4-dihydroisoquinoline (2a): 86% yield, known compound [ 54 ], yellow oil, Rf = 0.75 (ethyl acetate). 1H NMR (400 MHz, CDCl3) delta = 7.60-7.56 (m, 2H), 7.44-7.35 (m, 4H), 7.26-7.21 (m, 3H), 3.85-3.82 (m, 2H), 2.80-2.77 (m, 2H); 13C NMR (100 MHz, CDCl3) delta = 167.3, 139.0, 138.9, 130.7, 129.3, 128.9, 128.8, 128.1, 127.9, 127.4, 126.6, 47.7, 26.3.
22990-19-8, 22990-19-8 1-Phenyl-1,2,3,4-tetrahydroisoquinoline 100137, atetrahydroisoquinoline compound, is more and more widely used in various fields.
Reference£º
Article; Ji, Yue; Chen, Mu-Wang; Shi, Lei; Zhou, Yong-Gui; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 36; 1; (2015); p. 33 – 39;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem