Réaction #1605776

Équation de réaction

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

(2-methoxy-4-methylphenyl)methanamine

Et3N

ethyl 2-chloro-2-oxoacetate

→

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

Rendement 15.0%

Solvants

CH3CN

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
   TempératureAfter cooling the solvent
5. 5
   Autrewas removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   Lavagewashed successively with water and brine
8. 8
   Séchagedried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated
11. 11
    AutreThe residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    Autrerecrystallized from ethyl acetate/hexane and ethanol/water

Mode opératoire

A mixture of 2 g of (2-methoxy-4-methylphenyl)methanamine (from step 3) and Et3N (3.7 mL, 2 eq) in dry CH3CN (45 mL) was cooled to 0° C. under N2 atmosphere and ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 eq) was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 eq, from step 5) was added. The reaction was heated at reflux for 24 hours. After cooling the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane) and recrystallized from ethyl acetate/hexane and ethanol/water to give 650 mg of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide (15%).

Source