Reaction #1605769

Reaction equation

2-(2-pyridinyl)ethyl amine

2-Methoxybenzyl amine

triethylamine

Dioxane

→

title compound

Yield 70.0%

N-(2-Methoxy-benzyl)-N′-(2-pyridin-2-yl-ethyl)-oxalamide

Yield 70.0%

Conditions

Workup

1. 1
   Temperaturethe suspension was heated at 80° C. overnight
2. 2
   ConcentrationThe solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Washwashed with water
5. 5
   DryingThe organic layer was dried by sodium sulfate and solvent
6. 6
   Otherwas evaporated
7. 7
   Otherto give the crude product, which
8. 8
   Otherwas purified by flash column chromatography

Procedure

2-Methoxybenzyl amine (5 mmol) was mixed with triethylamine (2 equiv.) in anhydrous Dioxane. Ethyl oxalyl chloride (1 equiv.) was added and the mixture was shaken at room temperature for 0.5-2 hours. Then 2-(2-pyridinyl)ethyl amine (1 equiv.) was added and the suspension was heated at 80° C. overnight. The solution was concentrated and the residue was dissolved in ethyl acetate and washed with water. The organic layer was dried by sodium sulfate and solvent was evaporated to give the crude product, which was purified by flash column chromatography to afford the title compound: yield 70%, m.p. 118-119° C.; m/e=314 [M+1]; 1H NMR (CDCl3): 3.02 (t, 2H), 3.76 (dt, 2H), 3.86 (s, 3H), 4.47 (d, 2H), 6.80-6.90 (m, 2H), 7.14-7.18 (m, 2H), 7.20-7.30 (m, 2H), 7.55-7.62 (m, 1H), 7.75-7.83 (m, 1H), 8.05-8.12 (m, 1H), 8.55-8.63 (m, 1H).

Source