Реакция #1605776

Уравнение реакции

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

Выход 15.0%

Растворители

CH3CN

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition
2. 2
   ТемператураThe reaction was heated
3. 3
   Температураat reflux for 24 hours
4. 4
   ТемператураAfter cooling the solvent
5. 5
   Другоеwas removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   Промывкаwashed successively with water and brine
8. 8
   Сушкаdried over MgSO4
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated
11. 11
    ДругоеThe residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    Другоеrecrystallized from ethyl acetate/hexane and ethanol/water

Методика

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%).

Источник