Trifluoroacetic acid → HCID 60196780, compound

Participants

Reaction Steps

To a stirred solution of tert-Butyl 4-[3-fluoro-4-(2-(morpholin-4-yl)acetylamino) phenoxy]piperidine-1-carboxylate (3.1 g, 0.007 moles, obtained in above step) in dichloromethane (25 mL) was added trifluoroacetic acid (8.1 g, 0.071 moles) and stirred reaction mass overnight at room temperature. After completion of reaction, solvent was evaporated under vacuum and the residue, thus obtained, was basified with 10% caustic lye solution. Extracted the reaction mass with ethyl acetate twice, the combined organic layer dried over sodium sulphate and evaporated under reduced pressure. The crude product, thus obtained, was treated with cyclobutanone (0.6 g, 0.008 moles), in ethylene dichloride (30 mL), and stirred for 4 hours at room temperature. Sodium triacetoxyborohydride (3 g, 0.014 moles) was added to reaction mass in a single lot and the mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched in water and basified with lye solution. The layers were separated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were dried over sodium sulfate, concentrated under vacuum and the residual mass was further purified by flash chromatography (dichloromethane: triethylamine, 9.5:0.5) to obtain the title compound 1.52 g (Yield: 55%).

Provenance & Evidence