Acetone → HCID 15840426, compound

Participants

Reaction Steps

To a stirred solution of the hydrochloride salt of 1-(1-(4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (0.20 g, 0.30 mmol) from Example 2 in EtOH (3 mL) was added NaOAc (0.05 g, 0.6 mmol), acetone (0.027 mL, 0.37 mmol), powdered 3 angstrom molecular seives (approx. 100 mg). The mixture was stirred at ambient temperature for 1 h and NaBH3CN (0.021 mg, 0.34 mmol) was added. The mixture was stirred for 14 h at ambient temperature. More acetone (0.027 mL, 0.37 mmol), molecular seives (approx. 100 mg), and NaBH3CN (0.021 mg, 0.34 mmol) were added and the mixture was stirred at ambient temperature for 48 h. The mixture was diluted with EtOAc, filtered, and the solvents were removed under reduced pressure. The residue was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (2×25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was dissolved in EtOH (5 mL) and 1.5 equivalents of 6 N aqueous HCl was added. The solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (1 mL) and added to a rapidly stirred ether (20 mL). The precipitate was collected by filtration to give the hydrochloride salt of the title compound as an amorphous solid.

Provenance & Evidence