Dimethylformamide → HCID 54511705, compound

Participants

Reaction Steps

To a solution of 1.3 g (4.9 mmol) of (R)-3-(2, 3-methylenedioxyphenyl) octanoic acid in 20 ml of methylene chloride were added 1.1 ml of thionyl chloride and 0.1 ml of N, N-dimethylformamide, and the resultant mixture was refluxed under stirring for 2 hours. The reaction mixture was concentrated in vacuo to give (R)-3-(2, 3-methylenedioxyphenyl) octanoyl chloride as an oil. This oil was dissolved in methylene chloride to give a solution, which was dropwise added to a solution of 1.08 g (4.9 mmol) of 2, 6-diisopropyl-3-dimethylaniline and 1.0 ml of triethylamine in 20 ml of methylene chloride (5°-10° C.). The reaction mixture was allowed to react at room temperature overnight and chromatographed on a silica gel column, eluting with ethyl acetate/hexane to give 1.16 g of gelatinous material. This was dissolved in acetone and mixed with 22% solution of hydrogen chloride in 2 ml of ethyl acetate. The resultant mixture (hydrochloride) was concentrated and crystallized from hexane to give 1.23 g of (R)-N-(2, 6-diisopropyl-3-dimethylaminophenyl)-3-(2, 3-methylenedioxyphenyl) octanamide hydrochloride. Yield, 50%.

Provenance & Evidence