反应 #1605776

反应方程式

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

收率 15.0%

溶剂

CH3CN

反应条件

后处理

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
   其他was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   洗涤washed successively with water and brine
8. 8
   干燥dried over MgSO4
9. 9
   过滤filtered
10. 10
    其他evaporated
11. 11
    其他The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    其他recrystallized from ethyl acetate/hexane and ethanol/water

实验过程

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%).

来源