4-[(4-methoxyphenyl)methyl]morpholine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Methyoxybenzylchloride (25 g, 0.16 mol), morpholine (14 g, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) were taken up in acetonitrile and Kl (8.7 g, 0.04 mol) added. The reaction mixture was heated at reflux for 18 h, filtered, and the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil; IR(film, υ=cm−1) 2956, 2806, 1514, 1246, 1118, 866; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (4H, br. s), 3.35 (2H, s), 3.53 (4H, t, J=4.4 Hz), 3.71 (3H, s), 6.86 (2H, d, J=8.5 Hz), 7.19 (2H, d, J=8.5 Hz); MS(DCl)m/z: 208 (MH+). Kl (8.7 g, 0.04 mol) added The reaction mixture was heated at reflux for 18 h filtered the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Methyoxybenzylchloride (25 g, 0.16 mol), morpholine (14 g, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) were taken up in acetonitrile and Kl (8.7 g, 0.04 mol) added. The reaction mixture was heated at reflux for 18 h, filtered, and the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil; IR(film, υ=cm−1) 2956, 2806, 1514, 1246, 1118, 866; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (4H, br. s), 3.35 (2H, s), 3.53 (4H, t, J=4.4 Hz), 3.71 (3H, s), 6.86 (2H, d, J=8.5 Hz), 7.19 (2H, d, J=8.5 Hz); MS(DCl)m/z: 208 (MH+). Kl (8.7 g, 0.04 mol) added The reaction mixture was heated at reflux for 18 h filtered the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Methyoxybenzylchloride (25 g, 0.16 mol), morpholine (14 g, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) were taken up in acetonitrile and Kl (8.7 g, 0.04 mol) added. The reaction mixture was heated at reflux for 18 h, filtered, and the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil; IR(film, υ=cm−1) 2956, 2806, 1514, 1246, 1118, 866; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (4H, br. s), 3.35 (2H, s), 3.53 (4H, t, J=4.4 Hz), 3.71 (3H, s), 6.86 (2H, d, J=8.5 Hz), 7.19 (2H, d, J=8.5 Hz); MS(DCl)m/z: 208 (MH+). Kl (8.7 g, 0.04 mol) added The reaction mixture was heated at reflux for 18 h filtered the filtrate concentrated and azeotropped with benzene to give 17.5 g (88%) as an oil