반응 #1605776

반응 방정식

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

수율 15.0%

용매

CH3CN

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도The reaction was heated
3. 3
   온도at reflux for 24 hours
4. 4
   온도After cooling the solvent
5. 5
   기타was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   세척washed successively with water and brine
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    기타evaporated
11. 11
    기타The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    기타recrystallized from ethyl acetate/hexane and ethanol/water

실험 절차

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%).

출처