Reaktion #44809

Reaktionsgleichung

2-(4-morpholinyl)ethanamine

2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole

→

N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine

Ausbeute 86.2%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturthe reaction was heated
3. 3
   Temperaturat reflux for 17 hours
4. 4
   EinengenThe reaction was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Waschenwashed with water
7. 7
   SonstigeThe combined organic layers were dried
8. 8
   Einengenconcentrated
9. 9
   SonstigePurification by chromatography on silica gel using a gradient of methanol in dichloromethane

Vorschrift

A solution of 2-(4-morpholinyl)ethanamine (1 g, 7.4 mmol) in dichloromethane was stirred as a solution of 2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole (0.3 g, 0.74 mmol) in dichloromethane was added dropwise and the reaction was heated at reflux for 17 hours. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with water. The combined organic layers were dried and concentrated. Purification by chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.26 g of N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine; 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.08 (t, 2H), 3.96 (s, 2H), 3.67 (m, 4H), 3.03 (t, 2H), 2.78 (t, 2H), 2.51 (t, 2H), 2.43 (m, 4H) ppm.

Quelle