Ethanol → HCID 68117460, compound

Participants

Reaction Steps

To a stirred mixture of 900 mg. (3.3. mmole) of the aminoalcohol XXI and 1.7 g. (16.5 mmole) of triethylamine in 12 ml. of absolute ethanol was added, at room temperature and under nitrogen, a solution of 0.605 g. (5 mmole) of allyl bromide. After the addition had been completed, the reaction mixture was refluxed for eighteen hours and then evaporated to dryness. The residue was mixed with a 20% aqueous sodium carbonate solution and the resulting mixture extracted with several portions of ether. The combined ether extracts were dried over Na2SO4 and evaporated to yield 940 mg. of an oil which was dissolved in ether. The resulting solution was filtered through a celite-charcoal mixture and the filtrate concentrated at reduced pressure. The remaining oil was converted, in ether, into the hydrochloride salt. Recrystallization from a methanol-ether mixture yielded 600 mg. of a white solid melting at 244°-46° C. (dec.). Yield, 51.9%. The IR and NMR spectra were consistent with the structure.

Provenance & Evidence