Reaktion #1605779

Reaktionsgleichung

2-(5-methylpyridin-2-yl)ethanamine

(2-methoxy-4-methylphenyl)methanamine hydrochloride salt

triethylamine

ethyl 2-chloro-2-oxoacetate

→

N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide

Ausbeute 30.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperaturThe reaction was heated
3. 3
   Temperaturat reflux for 24 hours
4. 4
   SonstigeAfter removal of the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   Waschenwashed successively with water and brine
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    WaschenThe residue was washed with methyl t-butyl ether (20 mL)
11. 11
    Sonstigerecrystallized from ethanol

Vorschrift

To a mixture of 1.8 g of (2-methoxy-4-methylphenyl)methanamine hydrochloride salt and triethylamine (5.1 mL, 3 equiv.) in dry acetonitrile (45 mL) was added ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 equiv.) dropwise at 0° C. under nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 equiv.) was added. The reaction was heated at reflux for 24 hours. After removal of the solvent, the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and evaporated. The residue was washed with methyl t-butyl ether (20 mL) and recrystallized from ethanol to give 1.3 g of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide as a white powder (yield 30%).

Quelle