Diisopropylethylamine → HCID 86589867, compound

Participants

Reaction Conditions

Reaction Steps

4-(6-diethylcarbamoyl-2,3,4,5-tetrahydro-azepin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (30 mg, 0.079 mmol) was dissolved in methanol (20 mL) and 10% palladium on carbon (10% w/w) (˜30 mg) added. The mixture was shaken under a hydrogen atmosphere (50 psi) for 3 h . The catalyst was removed by filtration through Celite® and the solvent evaporated under vacuum. The residue was dissolved in ethyl acetate (10 mL) under nitrogen, cooled to −78° C. and hydrogen chloride was passed in for a few minutes. The solution was allowed to warmed at room temperature then evaporated to dryness overnight in a stream of dry nitrogen. The residue was dissolved in anhydrous dichloromethane (4 mL), N,N-diisopropylethylamine (5 eq, 70 mL) was added followed by a suspension of anthracene-9-carbonyl chloride (Intermediate 3, 0.088 mmol) in dichloromethane (0.175 mL). The thin layer chromatography (9:1 dichloromethane-methanol) showed a new UV spot at Rf 0.40. After 30 minutes, the solution was washed with a mixed sodium hydrogen carbonate/sodium hydroxide solution, dried over anhydrous sodium sulfate, evaporated and the residue purified by chromatography on silica gel eluting with a 1%-2.5%-5%-10% methanol-dichloromethane gradient to give the title compound (20.4 mg, 53%).

Provenance & Evidence