Water → 2-(4-Chlorophenoxy)-N-methylethan-1-amine

Participants

Reaction Steps

To a stirred solution of Intermediate 19 (0.84 g) in tetrahydrofuran (30 ml) at 0° C. was added lithium aluminium hydride (0.64 g). The reaction was stirred at room temperature for 3 h, followed by reflux for 2 h. On cooling water (0.64 ml), aqueous sodium hydroxide (15%, 0.64 ml) and water (1.9 ml) were added. The precipitates were removed by filtration and the filtrate diluted with ethyl acetate (30 ml) and extracted with aqueous hydrochloric acid (2M, 2×30 ml). The aqueous layer was basified to pH 12 with aqueous sodium hydroxide (2M), and extracted with methanol/dichloromethane (10%, 2×50 ml). The combined organic extracts were washed with brine (40 ml) dried over magnesium sulphate (2 g) and the solvent removed in vacuo to yield the title compound as a pale yellow oil (0.32 g).

Provenance & Evidence