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

HRID 505355노트

반응식

HRID 505355 반응식
[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

참가 물질

6

반응물 3

HCID 8438Piperonal3회HCID 24083Sulfuric acid magnesium salt (1:1)HCID 89728Aminoacetaldehyde dimethyl acetal

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-24e30e740f544fb580dab4733e1b3b4d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781445B2

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