反応 #1605776

反応方程式

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

収率 15.0%

溶媒

CH3CN

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   温度The reaction was heated
3. 3
   温度at reflux for 24 hours
4. 4
   温度After cooling the solvent
5. 5
   その他was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   洗浄washed successively with water and brine
8. 8
   乾燥dried over MgSO4
9. 9
   ろ過filtered
10. 10
    その他evaporated
11. 11
    その他The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    その他recrystallized from ethyl acetate/hexane and ethanol/water

実験手順

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%).

出典