Réaction #1605769

Équation de réaction

2-(2-pyridinyl)ethyl amine

2-Methoxybenzyl amine

triethylamine

Dioxane

→

title compound

Rendement 70.0%

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

Rendement 70.0%

Conditions de réaction

Traitement

1. 1
   Températurethe 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
   Lavagewashed with water
5. 5
   SéchageThe organic layer was dried by sodium sulfate and solvent
6. 6
   Autrewas evaporated
7. 7
   Autreto give the crude product, which
8. 8
   Autrewas purified by flash column chromatography

Mode opératoire

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