6-Phenyl-1,2,3,4-tetrahydroisoquinoline → 3-(6-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-1H-pyrrolo[2,3-b]pyridine

関与物質

反応手順

A mixture of 6-phenyl-1,2,3,4-tetrahydroisoquinoline (prepared by the method of L. N. Pridgen, J. Heterocyclic Chem. 1980, 17, 1289) (0.5 g, 2.38 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.4 g, 2.28 mmol) in toluene (5 ml) was heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from ethyl acetate afforded the title compound (0.13 g, 17%), m.p. 211°-213° C.; (Found: C, 80.15; H, 6.30; N, 12.32. C23H21N3.0.3H2O requires C, 80.11; H, 6.31; N, 12.18%); δH (DMSO-d6) 2.73 (2H, br s, CH2CH2Ph), 2.87 (2H, br s, NCH2CH2), 3.61 (2H, s, ArCH2N), 3.83 (2H, s, NCH2Ph), 7.02 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.18 (1H, d, J 3.2 Hz, 2-H), 7.30-7.45 (6H, m, ArH), 7.60 (2H, d, J 7.6 Hz, ArH), 8.05 (1H, d, J 7.6 Hz, 4-H), 8.20 (1H, dd, J 6.1, 1.4 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 340 (M+1)+.

情報源と証拠