Reaktion #59445

Reaktionsgleichung

Cesium carbonate

2-(dimethylamino)ethyl chloride

2-phenylchroman-6-ol

→

Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

Lösungsmittel

ethyl acetate

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 30 minutes
2. 2
   SonstigeAfter removing the solvents
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe combined organic layers were washed with water
5. 5
   Trocknenwith saturated NaCl-solution and dried with Na2SO4
6. 6
   SonstigeThe dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane

Vorschrift

Cesium carbonate (230 mg) and an excess of 2-(dimethylamino)ethyl chloride in ethyl acetate were added into a solution of 2-phenylchroman-6-ol (150 mg) in acetonitrile (5 ml). The reaction mixture was refluxed for 30 minutes. After removing the solvents, the residue was taken up in water and extracted with ethyl acetate. The combined organic layers were washed with water and then with saturated NaCl-solution and dried with Na2SO4. The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane. 1H NMR (400 MHz, d6-DMSO) δ: 7.43-7.30 (m, 5H), 6.75-6.67 (m, 3H), 5.03 (dd, 1H, J 10.0, 2.2 Hz), 3.95 (t, 2H, J 5.9 Hz), 2.94 (ddd, 1H, J −16.7, 10.9, 5.8 Hz), 2.69 (ddd, 1H, J −16.7, 5.2, 3.3 Hz), 2.58 (t, 2H, J 5.9 Hz), 2.13 (m, 1H), 1.96 (m, 1H).

Quelle