1-Bromo-2-butanone → HCID 68981131, compound

Participants

Reaction Steps

2-Pyridinepropaneamide (6.5 g, 43 mmol) was dissolved in warm acetone (500 mL). 1-Bromobutanone (10.0 g, 66 mmol) was added and the reaction mixture was heated under reflux for 48 hours. The reaction mixture was cooled in a freezer and the acetone was decanted from a light brown solid (12 g). The solid was dissolved in hot ethanol (450 mL). Solid NaHCO3 (10 g) was added and the reaction mixture was heated under reflux with stirring for 6 h. The reaction mixture was filtered to remove NaBr and the filtrate was evaporated under reduced pressure to give a brown solid residue. The residue was extracted 4 times with boiling hexane (500 mL). Each time the solvent was decanted from the remaining solid and cooled in the freezer. A final extraction was with boiling heptane (500 mL). Collection of the cooled filtrates and drying of the collected solid gave 1.35 g of 2-(2-ethylindolizin-1-yl)acetamide. The 2-(2-ethylindolizin-1-yl)acetamide (440 mg ) in ethyl ether (90 mL) was treated with lithium aluminum hydride (360 mg) and heated under reflux in a nitrogen atmosphere overnight. After cooling to room temperature, an aqueous solution of Rochelle salt was cautiously added with stirring until a solution was observed. The phases were separated and the aqueous phase was extracted 3 times with ether. The combined organic layers were extracted with 0.1 N HCl, and the aqueous layer was made basic with 2.5 N NaOH. The aqueous phase was extracted with methylene chloride 3 times and the organic phase was evaporated under reduced pressure to give 410 mg of product as a yellow brown oil. The product (170 mg, 0.90 mmol) was dissolved in ethanol and treated with fumaric acid (52 mg, 0.45 mmol). The title compound was obtained as a golden brown solid, mp: 170-175° C. dec. MS [M+H]+ 189 m/z; microanalysis was consistent for C12H16N2+C4H4O4.

Provenance & Evidence