Hydrochloric Acid → HCID 12988961, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of trifluoro-methanesulfonic acid 3-(1-propyl-piperidin-4-yl)-phenyl ester (300 mg) in DMF (4 ml) under argon atm at r.t. was subsequently added NEt3 (356 μL), butyl vinyl ether (823 μL), 1,3-bis(diphenylphosphino)propane (50 mg), and Pd(OAc)2 (19 mg). The reaction mixture was then heated to 80° C. and after 2 h the reaction was stopped. 5% Hydrochloric acid solution (6 ml) was added and the combined mixture stirred for 45 min. Then CH2Cl2 was added and the phases were separated. The aqueous layer was then extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeOH:CH2Cl2 (1:9 (v/v)). Collection of the fractions containing pure product and evaporation of the solvent afforded pure 1-[3-(1-Propyl-piperidin-4-yl)-phenyl]-ethanone (35 mg). MS m/z (rel. intensity, 70 eV) 245 (M+, 4), 216 (bp), 100 (19), 70 (36), 57 (13).

Provenance & Evidence