Reaktion #1605769

Reaktionsgleichung

2-(2-pyridinyl)ethyl amine

2-Methoxybenzyl amine

triethylamine

Dioxane

→

title compound

Ausbeute 70.0%

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

Ausbeute 70.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe suspension was heated at 80° C. overnight
2. 2
   EinengenThe solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Waschenwashed with water
5. 5
   TrocknenThe organic layer was dried by sodium sulfate and solvent
6. 6
   Sonstigewas evaporated
7. 7
   Sonstigeto give the crude product, which
8. 8
   Sonstigewas purified by flash column chromatography

Vorschrift

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).

Quelle