Reaction #1605779

Reaction equation

2-(5-methylpyridin-2-yl)ethanamine

(2-methoxy-4-methylphenyl)methanamine hydrochloride salt

triethylamine

ethyl 2-chloro-2-oxoacetate

→

N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide

Yield 30.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperatureThe reaction was heated
3. 3
   Temperatureat reflux for 24 hours
4. 4
   OtherAfter removal of the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   Washwashed successively with water and brine
7. 7
   Dryingdried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated
10. 10
    WashThe residue was washed with methyl t-butyl ether (20 mL)
11. 11
    Otherrecrystallized from ethanol

Procedure

To a mixture of 1.8 g of (2-methoxy-4-methylphenyl)methanamine hydrochloride salt and triethylamine (5.1 mL, 3 equiv.) in dry acetonitrile (45 mL) was added ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 equiv.) dropwise at 0° C. under nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 equiv.) was added. The reaction was heated at reflux for 24 hours. After removal of the solvent, the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and evaporated. The residue was washed with methyl t-butyl ether (20 mL) and recrystallized from ethanol to give 1.3 g of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide as a white powder (yield 30%).

Source