Water → HCID 9864130, compound

Participants

Reaction Steps

N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-FMOC-piperazin-1-yl)-benzamide (4.4 mmol) is dissolved in DMF (15 ml), piperidine (4.4 mmol) is added and the mixture is stirred at RT for 4 hours. 4 additional drops of piperidine are added and the mixture is stirred over night. The reaction mixture is poured into water and ethyl acetate and the suspension is filtered and the filtrate is acidified with HCl 4N and then extracted with ethyl acetate. Saturated sodium carbonate solution is added to make the water phase basic and the mixture is extracted three times with ethyl acetate. The water phase is saturated with sodium chloride and extracted three times with ethyl acetate again. The organic fractions are dried over sodium sulfate and the solvent is evaporated. The residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH (with 3N NH3)=95:5 as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 206-210° C., Rf=0.28 (CH2Cl2/MeOH (with 3N NH3)=9:1) is obtained.

Provenance & Evidence