Piperonal → (3,4-Methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine

Participants

Reaction Steps

Aminoacetaldehyde dimethylacetal (7.10 g, 0.0666 mol) was dissolved in chloroform (50 mL) and MgSO4 (12 g) was added. Then piperonal (10b, 10.10 g, 0.0666 mol) was added and the mixture was stirred at room temperature. After 24 h there still was unreacted piperonal in the reaction mixture and more amine (6.00 g) was added. The reaction mixture was stirred again at room temperature for 24 h and since there still was some piperonal present more amine (6.00 g) was added again. After stirring the reaction mixture for another 24 h at room temperature the imine was isolated. The reaction mixture was diluted with water (300 mL) and the organic layer was washed with water 200 mL×2, brine (200 mL) dried Na2SO4 and concentrated to provide the pure imine as a yellow oil (15.80 g, 100%). 1H NMR (300 MHz, CDCl3) δ 8.13 (s, 1H), 7.33 (s, 1H), 7.07 (d, J=8.10 Hz, 1H), 6.78 (d, J=8.10 Hz, 1H), 5.96 (s, 2H), 4.62 (t, J=5.4 Hz, 1H), 3.70 (d, J=4.2, 2H), 3.83 (s, 6H).

Provenance & Evidence