Reaction Steps
Methanesulfonic acid (0.14 ml, 2.16 mmol) was added to a solution of (E)-3-[4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridin-1-yl]methylbenzo[b]furan (0.6817 g, 2.16 mmol) in ethyl acetate (15 ml) to give a white precipitate. The solid was collected under suction, washed with ethyl acetate and recrystallised from 2-propanol to afford the title compound (0.6979 g, 78%), m.p. 216.5°-218° C. (dec.); (Found: C, 67.04; H, 6.08; N, 3.44. C23H25NO4S requires C, 67.13; H, 6.13; N, 3.40%); δH (500MHz, DMSO-d6) 2.43 (3H, s, CH3SO3), 2.66 (2H, m, tetrahydropyridinyl CH2), 3.29 (1H, m, tetrahydropyridinyl CH2), 3.71 (1H, m, tetrahydropyridinyl CH2), 3.90 (2H, m, tetrahydropyridinyl CH2), 4.60 (2H, br s, ArCH2N), 5.90 (1H, s, tetrahyropyridinyl CH), 6.61 (1H, d, J 16.3Hz, CH=CHPh), 6.97 (1H, d, J 16.3Hz, CH=CHPh), 7.24 (1H, t, J 7.3Hz, ArH), 7.31-7.42 (4H, m, ArH), 7.50 (2H, d, J 7.5Hz, ArH), 7.66 (1H, d, J 7.7Hz, ArH), 7.93 (1H, d, J 7.2Hz, ArH), 8.25 (1H, s, 2-H), 10.01 (1H, br s, NH+); m/z (ES+) 316 [(M+H)+ ].
