Acetic Acid → HCID 21109896, compound

Participants

Reaction Steps

To a solution of 27.8 g (0.15 mol) of 1-(phenylmethyl)-4-piperidinone and 26.5 g (0.15 mol) of 1-(3-dimethylaminopropyl)-piperazine in 500 ml of tetrahydrofuran were added 200 mg of p-toluenesulphonic acid and 13.5 g (0.225 mol) of glacial acetic acid, followed by 47.7 g (0.225 mol) of sodium triacetoxyborohydride, in small batches, and the mixture was stirred overnight at ambient temperature. 100 ml of water were added dropwise while stirring was continued and after 30 minutes sufficient potassium carbonate was added to produce a precipitate that could be filtered off. It was filtered and the filter cake was washed thoroughly with THF and diethylether in succession. The combined filtrates were concentrated by evaporation in vacuo, the residue was purified by column chromatography on 400 g of aluminium oxide (Al2O3—ICN, activity stage 3) using EE/MeOH (95/5 v/v) as eluant. A colourless oil, Rf 0.33 (El O), was obtained in a yield of 35.0 g (68% of theoretical). MS: ESI: (M+H)+=345

Provenance & Evidence