Diisopropylethylamine → HCID 10177192, compound

Participants

Reaction Steps

4-Cyclohexylbenzoic acid (0.50 g, 2.45 mmol) was suspended in thionyl chloride (3 mL) and heated at reflux for 30 minutes. After cooling, the thionyl chloride was removed in vacuo. The residue was dissolved in toluene and concentrated in vacuo to give the crude acid chloride as a yellow oil which was then dissolved in dichloromethane (5 mL) and slowly added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.67 g, 3.64 mmol) and N,N-diisopropylethyl amine (0.94 mL, 5.4 mmol) in dichloromethane (15 mL). After stirring for 2 hours, the reaction was quenched with water. The organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. Purification by flash chromatography using a solvent system of 50% dichloromethane in hexane followed by 25% ethyl acetate in hexane gave a white foam which crystallized upon sonication from hexane/ethyl acetate to provide the title compound (0.60 g) as a white solid, m.p. 127–129° C.

Provenance & Evidence