Trifluoroacetic acid → 1'-(2,2,2-Trifluoroethyl)-spiro[indoline-3,4'-piperidin]-2-one

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Reaction Steps

A mixture of spiro[indoline-3,4′-piperidin]-2-one, [PCT Int. Appl. WO 0145707 A1 (2001)] trifluoroacetic acid salt (3.66 g, 11.6 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.63 mL, 11.6 mmol), and triethylamine (8.06 mL, 57.9 mmol) in acetone (30 mL) was heated at reflux for 16 h. The mixture was allowed to cool, and the solvent removed under reduced pressure. The residue was taken up in CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was further extracted with CH2Cl2 (2×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=285 (M+1).

Provenance & Evidence