Реакция #44809

Уравнение реакции

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

Выход 86.2%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Температураthe reaction was heated
3. 3
   Температураat reflux for 17 hours
4. 4
   КонцентрированиеThe reaction was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Промывкаwashed with water
7. 7
   ДругоеThe combined organic layers were dried
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

Методика

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.

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