Dimethylformamide → HCID 54511706, compound

Participants

Reaction Steps

To a solution of 2.64 g (10 mmol) of 3-(2, 3-methylenedioxyphenyl)octanoic acid in 25 ml of methylene chloride were added 1.46 ml (20 mmol) of thionyl chloride and 0.1 ml of N, N-dimethylformamide, and the resultant mixture was stirred at room temperature for 4 hours and concentrated in vacuo to give 3-(2, 3-methylenedioxyphenyl)octanoic acid chloride as a crude oil. A solution of this acid chloride in 15 ml of methylene chloride was dropwise added to a solution of 1.95 g (11 mmol) of 2, 6-diisopropylaniline and 1.67 ml (12 mmol) of triethylamine in 40 ml of methylene chloride chilled with water under stirring. Stirring was continued for 2 hours, and the reaction mixture was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/6) and crystallized from hexane to give 3.60 g (Yield, 85%) of N-(2, 6-diisopropylphenyl)-3-(2, 3-methylenedioxyphenyl)octanamide as white crystals,

Provenance & Evidence