Methylamine → N-methyl-3,4-dimethoxycinnamylamine

HRID 1282925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282925
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:6]=[CH:7][CH:8]=O.S([O-])([O-])(=O)=O.[Mg+2].[CH3:21][NH2:22]>C1C=CC=CC=1>[CH3:21][NH:22][CH2:8][CH:7]=[CH:6][C:5]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1075573-(3,4-Dimethoxyphenyl)-2-propenal

Produkt 1

HCID 53660943N-methyl-3,4-dimethoxycinnamylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

The starting material is prepared as follows: To the mixture of 19.2 g of 3,4-dimethoxycinnamaldehyde, 24 g of magnesium sulfate and 100 ml of benzene, 6.2 g of methylamine in 120 ml of benzene are added and the suspension is stirred at room temperature for 8 hours. It is filtered and the filtrate added dropwise to the solution of 3.8 g of sodium borohydride in 200 ml to anhydrous ethanol while stirring and cooling with ice. Stirring is continued over night at room temperature, the mixture cooled again, 25 ml of concentrated hydrochloric acid are added and the solution evaporated under reduced pressure. The residue is taken up in 150 ml of water the solution washed with diethyl ether, made basic with sodium hydroxide and the mixture extracted with diethyl ether. The extract is dried and evaporated, to yield the N-methyl-3,4-dimethoxycinnamylamine as an oil; the cyclamate thereof melts at 145°-147°.

Aufarbeitung

  1. customThe starting material is prepared
  2. additionare added
  3. filtrationIt is filtered
  4. additionthe filtrate added dropwise to the solution of 3.8 g of sodium borohydride in 200 ml to anhydrous ethanol
  5. stirringwhile stirring
  6. temperaturecooling with ice
  7. stirringStirring
  8. waitis continued over night at room temperature
  9. temperaturethe mixture cooled again
  10. addition25 ml of concentrated hydrochloric acid are added
  11. customthe solution evaporated under reduced pressure
  12. washwashed with diethyl ether
  13. extractionthe mixture extracted with diethyl ether
  14. customThe extract is dried
  15. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-63bbb5edd6e344c483f1207b97562ead
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03973030

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