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

HRID 505355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505355
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[O-]S([O-])(=O)=O.[Mg+2].[CH:14]1[C:19]([CH:20]=O)=[CH:18][C:17]2[O:22][CH2:23][O:24][C:16]=2[CH:15]=1>C(Cl)(Cl)Cl.O>[CH2:23]1[O:24][C:16]2[CH:15]=[CH:14][C:19]([CH:20]=[N:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[CH:18][C:17]=2[O:22]1

Komponenten

6

Edukt 3

HCID 8438Piperonal3×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 89728Aminoacetaldehyde dimethyl acetal

Produkt 1

HCID 11149084(3,4-Methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. stirringThe reaction mixture was stirred again at room temperature for 24 h
  2. additionwas added again
  3. customwas isolated
  4. washthe organic layer was washed with water 200 mL×2, brine (200 mL) dried Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-24e30e740f544fb580dab4733e1b3b4d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781445B2

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