Reaction #44809

Reaction equation

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

Yield 86.2%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturethe reaction was heated
3. 3
   Temperatureat reflux for 17 hours
4. 4
   ConcentrationThe reaction was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Washwashed with water
7. 7
   OtherThe combined organic layers were dried
8. 8
   Concentrationconcentrated
9. 9
   OtherPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

Procedure

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.

Source