Reaction Steps
Concentrated HCl (20 mL) was added to a mixture of (3,4-methylenedioxybenzyl)-(2,2-dimethoxyethyl)amine (12b, 1.79 g, 7.49 mmol) and veratraldehyde (10a, 3.04 g, 0.018 mol). The reaction mixture was stirred at 100° C. for 3 h. The reaction mixture was then cooled and washed with ether (50 mL×3). Then it was brought to a basic pH with NH4OH. The mixture was extracted with chloroform (50 mL×4), washed with water (100 mL), dried (Na2SO4) and concentrated. The residue was dissolved in an organic solvent (200 mL chloroform). The mixture was filtered and HCl (2 M in ether, 40 mL) was added to the filtrate. The yellow precipitate that formed (0.7649 g, 29%) was collected by filtration. An analytical sample was prepared by recrystallizing 0.3655 g from methanol (50 mL), mp 257-259° C. 1H NMR (300 MHz, TFA) δ 8.88 (s, 1H), 7.69 (s, 1H), 7.39 (s, 1H), 7.33 (s, 2H), 6.21 (s, 2H), 4.18 (s, 2H), 4.02 (s, 3H), 4.01 (s, 3H); low resolution ESIMS m/z (rel intensity) 322 (100, MH+); high resolution ESIMS m/z (rel intensity) 322.1084 (100, MH+) (calculated mass 322.1079); IR (KBr) 3435, 3043, 2966, 2841, 2648, 2027, 1623, 1589, 1494, 1470, 1458, 1419, 1379, 1323, 1291, 1275, 1256, 1220, 1198, 1147, 1122, 1092, 1035, 969, 935, 902, 872, 835, 818, 785, 762, 743, 572 cm−1. Anal. Calcd for C19H16NO4Cl(H2O)0.7: C, 61.61; H, 4.74; N, 3.78. Found: C, 61.40; H, 4.98; N, 3.75.
