Hydrochloric Acid → HCID 86761160, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (20 mL) was added to a mixture of amine 12a (2.17 g, 8.51 mmol) and piperonal (10b, 3.0 g, 0.020 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 a mixture of organic solvents (50 mL diethyl ether, 100 mL dichloromethane, 100 mL chloroform). The mixture was filtered and HCl (2 M in ether, 40 mL) was added to the filtrate. The yellow precipitate that formed (0.806 g, 26%) was collected by filtration, mp 238-240° C. 1H NMR (300 MHz D2O) δ 8.30 (s, 1H), 6.91 (s, 1H), 6.69 (s, 1H), 6.44 (s, 1H), 6.39 (s, 1H), 5.94 (s, 2H), 3.78 (s, 3H), 3.77 (s, 3H), 3.00 (s, 2H); low resolution ESIMS m/z (rel intensity) 322 (100, M+); IR (KBr) 3429, 3032, 2611, 1623, 1551, 1504, 1489, 1430, 1413, 1379, 1331, 1296, 1273, 1226, 1206, 1172, 1036, 977, 933, 837, 776, 724 cm−1. Anal. Calcd for C19H16NO4Cl(H2O)0.85: C, 61.17; H, 4.78; N, 3.75. Found: C, 61.19; H, 4.77; N, 3.56.

Provenance & Evidence