Reaction Steps
A solution of 4-(2-[furan-2-yl]ethyl)-1,2,3,6-tetrahydropyridine (506 mg, 2.86 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.86 mmol) in toluene (10 ml) was stirred at reflux for 10 hours. The solvent was evaporated and the residue chromatographed with 3% methanol in dichloromethane as eluant to afford the title compound (200 mg, 23%) as a colourless solid, m.p. 105° C.; (Found: C, 73.84; H, 6.72; N, 13.31. C19H21N3O requires C, 74.24; H, 6.89; N, 13.67); δH (DMSO-d6) 2.00-2.06 (2H, m, tetrahydropyridinyl CH2), 2.22 (2H, t, J 7.7 Hz, CH2), 2.48-2.54 (2H, m, CH2), 2.68 (2H, t, J 7.3 Hz, tetrahydropyridinyl CH2), 2.84-2.89 (2H, m, tetrahydropyridinyl CH2), 3.66 (2H, s, NCH2Ar), 5.34-5.38 (1H, m, tetrahydropyridinyl 5-H), 6.06 (1H, d, J 2.9 Hz, furanyl 3-H), 6.31 (1H, dd, J 3.0, 1.9 Hz, furanyl 4-H), 7.02 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.32 (1H, d, J 2.3 Hz, furanyl 5-H), 7.46 (1H, d, J 3.0 Hz, 2-H), 7.99 (1H, m, dd, J 7.8, 4.1 Hz, 4-H), 8.18 (1H, dd, J 4.6, 1.4 Hz, 6-H), and 11.38 (1H, br s, NH); m/z (CI+, NH3) 308 (M+1)+.
