Water → HCID 15572626, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[α-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine (7.35 g) in CHCl3 (50 ml), 2 N NaOH (18.2 ml) was added; the mixture was cooled to 0° C. and ethyl chloroformiate (3.5 ml) was dropped over 30 minutes. Stirring and cooling at 0° C. was maintained for 1 hour; the organic phase was separated, washed with water and dried over anhydrous CaCl2. The evaporation to dryness of the solvent gave a colourless oil which was dissolved in diethyl ether (100 ml) and added, at room temperature, to a suspension of LiAlH4 (2.5 g) in anhydrous diethyl ether (200 ml). The mixture was stirred at room temperature for 20 hours; water (2.5 ml), 15% NaOH (2.5 ml) and water (7.5 ml) were added. After filtration, the ethereal layer was separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water and dried over anhydrous Na2SO4. After evaporation to dryness of the solvent, 4-methyl-2-[α-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine was obtained as oil (6.25 g; yield 82%). Analogously, all the 4-methyl-morpholine derivatives of the Example 17 were prepared.

Provenance & Evidence