تفاعل #1605776

معادلة التفاعل

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

المردود 15.0%

المذيبات

CH3CN

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   درجة الحرارةThe reaction was heated
3. 3
   درجة الحرارةat reflux for 24 hours
4. 4
   درجة الحرارةAfter cooling the solvent
5. 5
   أخرىwas removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
7. 7
   غسيلwashed successively with water and brine
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    أخرىevaporated
11. 11
    أخرىThe residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
12. 12
    أخرىrecrystallized from ethyl acetate/hexane and ethanol/water

الإجراء التجريبي

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%).

المصدر