Sodium hydride → (+/-)-trans-4-BENZYL-2-[2-(3,5-BIS-TRIFLUOROMETHYLPHENYL)-ETHOXY]-3-(4-FLUOROPHENYL)MORPHOLINE

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Reaction Conditions

Reaction Steps

3.76 g of sodium hydride and 300 ml of dimethylsulfoxide (DMSO) were charged into a clean and dry 4neck round bottom flask under nitrogen atmosphere, followed by heating to about 70° C. and was stirred for about 2 hours. Resultant reaction solution was cooled to about 30° C. and a solution of 30 g of (±)-N-benzyl-3-(4-fluorophenyl)-1,4-oxazin-2-ol of Formula VIII dissolved in 60 ml of dimethyl sulfoxide, a solution of 50 g of 1-(1-bromoethyl) 3,5-bis-trifluoromethyl-benzene of Formula VII dissolved in 60 ml of dimethylsulfoxide were charged followed by stirring for about 3 hours. After completion of the reaction, the reaction mass was quenched with 450 ml of precooled water and 300 ml of toluene. Organic and aqueous phases were separated and the aqueous phase was extracted with 2×300 ml of toluene. Combined organic layer was washed with 3×300 ml of water followed by drying the organic layer over 100 g of anhydrous sodium sulphate and the organic layer was distilled completely at about 60° C. under vacuum to afford 40 g of the title compound.

Provenance & Evidence