Réaction #1605779

Équation de réaction

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

Rendement 30.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TempératureThe reaction was heated
3. 3
   Températureat reflux for 24 hours
4. 4
   AutreAfter removal of the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   Lavagewashed successively with water and brine
7. 7
   Séchagedried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated
10. 10
    LavageThe residue was washed with methyl t-butyl ether (20 mL)
11. 11
    Autrerecrystallized from ethanol

Mode opératoire

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%).

Source