2-Iodotoluene → N,N-Dimethyl-3-phenyl-3-(o-tolyloxy)propan-1-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of N,N-dimethyl-3-hydroxy-3-phenylpropylamine (0.9 g, 5 mmol), 2-iodotoluene (1.31 g, 6 mmol), cuprous iodide (0.2 g) and cesium carbonate (1.8 g, 5.5 mmol) was stirred under nitrogen at 130° C. until the reaction was complete as determined by 1H NMR. The reaction mixture was cooled to room temperature, diluted with methyl t-butyl ether (10 mL), filtered, and rinsed with more methyl t-butyl ether. The filtrate was extracted with diluted hydrochloric acid solution and the aqueous layer was washed with more methyl t-butyl ether. The aqueous was adjusted to pH>10 by the addition of sodium hydroxide solution, then extracted with methyl t-butyl ether twice. The combined extracts were washed with water and then evaporated to dryness to give 1.2 g of N,N-dimethyl-3-(2-methylphenoxy)-3-phenylpropylamine as a light yellow oil. 1H NMR (CDCl3) δ 7.45-7.2 (m, 5H), 7.12 (d, J=6.8 Hz, 1H), 7.0 (dd, J=8.0, 7.6 Hz, 1H), 6.78 (dd, J=8.4, 6.8 Hz, 1H), 6.63 (d, J=8.1 Hz, 1H), 5.24 (dd, J=8.1, 4.8 Hz, 1H), 2.46 (t, J=7.3 Hz, 2H), 2.33 (s, 3H), 2.24 (s, 6H), 2.3-2.1 (m, 1H), 2.05-1.9 (m, 1H).

Provenance & Evidence