Reacción #1605769

Ecuación de reacción

2-(2-pyridinyl)ethyl amine

2-Methoxybenzyl amine

triethylamine

Dioxane

→

title compound

Rendimiento 70.0%

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

Rendimiento 70.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe suspension was heated at 80° C. overnight
2. 2
   ConcentraciónThe solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Lavadowashed with water
5. 5
   SecadoThe organic layer was dried by sodium sulfate and solvent
6. 6
   Otrowas evaporated
7. 7
   Otroto give the crude product, which
8. 8
   Otrowas purified by flash column chromatography

Procedimiento

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).

Fuente