Triethylamine → (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamide

HRID 428129

Reaktionsgleichung

Reaktionsgleichung von HRID 428129
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](/[CH:23]=[CH:24]/[C:25](O)=[O:26])[CH:18]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)[C:25](=[O:26])/[CH:24]=[CH:23]/[C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 138365N-MethylmescalineHCID 516892Sodium BicarbonateHCID 776396trans-3-(3-Pyridyl)acrylic acid

Produkt 1

HCID 23067296(E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-Methyl-3,4,5-trimethoxyphenethylamine (1.60 g, 7.11 mmol) and trans-3-(3-pyridyl)acrylic acid (1.17 g) were dissolved in dimethylformamide (8 ml), and diethylphosphoric cyanide (1.3 ml) and triethylamine (2.2 ml) were sequentially added under ice-cooling and stirring and stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the reaction mixture was extracted with dichloromethane, washed with water and dried over potassium carbonate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1) to yield amorphous (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenoic acid amide (2.37 g, 94%). Then, hydrogen chloride-methanol was added to the product (1.80 g) to produce its hydrochloride, which was recrystallized in a mixed solvent of ethyl acetate-methanol to yield the titled compound (1.59 g, 57%).

Aufarbeitung

  1. temperaturecooling
  2. stirringstirred at room temperature for 1 hour
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over potassium carbonate
  6. distillationThe solvent was distilled out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c2f9a2806f274d10848e86d2d0cd1129
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313153B1

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