Diethyl Ether → HCID 20080542, compound

Participants

Reaction Conditions

Reaction Steps

9 g of 7-cyanooctanoic acid dicyclohexylamine salt is added to a mixture of 28 cm3 of a molar solution of sodium hydrogen sulphate and 60 cm3 of diethyl ether. The mixture is stirred for 15 minutes at 20° C. and the organic phase is then separated. The latter is dried over magnesium sulphate and filtered and the solvent is evaporated off under reduced pressure. The residue is treated with 14.8 g of thionyl chloride and heated to 50° C. for 3 hours. The mixture is concentrated under reduced pressure. The residual oil is dissolved in 6 cm3 of dichloromethane, and the solution obtained is added to a suspension, stirred and cooled to 5° C. of 6 g of 2-amino-1,2-diphenylethanone hydrochloride in 30 cm3 of dichloromethane containing 4.8 g of pyridine. After treatment, the product obtained is chromatographed on a column 2 cm in diameter containing 48 g of silica gel (50 to 200μ). The column is eluted, collecting 100 cm3 fractions, with 1.2 liters of a diisopropyl ether/ethyl acetate (80:20 by volume) mixture. The fractions emerging at between 0.3 and 1.2 liters are concentrated under reduced pressure (0.2 kPa). 5.9 g (67%) of (RS) -1,2-diphenyl-2-(7-cyanooctanamido)ethanone are obtained in the form of an oil, which is used directly in the subsequent reaction.

Provenance & Evidence