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ChemicalBook CAS DataBase List N-[4-(Morpholin-4-yl)phenyl]acetaMide
103913-29-7

N-[4-(Morpholin-4-yl)phenyl]acetaMide synthesis

11synthesis methods
-

Yield: 89%

Reaction Conditions:

with potassium carbonate;potassium iodide in acetonitrile at 90; for 24 h;

Steps:

3 4.3. N-(4-morpholinophenyl)acetamide (4)
A solution of 4′-aminoacetanilide (100 mg, 0.665 mmol), bis(bromoethyl)ether (635 μL, 0.505 mmol), potassium iodide (188 mg,1.13 mmol) and potassium carbonate (156 mg, 1.13 mmol) in 15.0 mLacetonitrile was heated at 90 °C for 24 h, and then was cooled to roomtemperature and filtered. The filtrate was concentrated and purified bysilica gel column chromatography (CH2Cl2: methanol=15: 1) to afforda solid product (130.4 mg, 89%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d J=8.8 Hz, 2H), 7.26 (br, 1H), 6.87 (d, J=8.8 Hz, 2H), 3.85 (t,J=4.8 Hz, 4H), 3.11 (t, J=4.8 Hz, 4H), 2.14 (s, 3H); 13C NMR(125 MHz, CDCl3) δ 168.3, 148.4, 130.8, 121.7, 116.4, 67.0, 47.9, 24.5.; FT-IR (neat) 3276, 3190, 3119, 2958, 2848, 2826, 1654, 1533, 1456,1119 cm-1; Mp 208 °C ; HRMS (ESI, positive): calcd. for[C12H16N2O2+H]+: 221.1285, found 221.1286

References:

Sato, Shinichi;Yoshida, Masaki;Hatano, Kensuke;Matsumura, Masaki;Nakamura, Hiroyuki [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 6,p. 1110 - 1118]