Diisopropylethylamine → tert-Butyl 4-(3-(tert-butylcarbamoyl)benzyl)-1,4-diazepane-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl-1-homopiperazine carboxylate (0.25 g, 1.25 mmol) and N-tert-butyl-3-(chloromethyl)benzamide (0.470 g, 1.25 mmol) in tetrahydrofuran (4 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.33 mL, 1.88 mmol). The resultant mixture was stirred at 80° C. for 16 hours. The mixture was cooled to room temperature, diluted with dichloromethane (50 mL) and washed with saturated ammonium chloride (aqueous) and brine. The organic phase was dried (sodium sulfate), filtered and concentrated under vacuum. The residue was purified by column chromatography on silica (using a solvent gradient of dichloromethane/methanol) to afford the title compound (0.435 g) as a white solid. MS (ESI) m/z 389.9 [M+H]+

Provenance & Evidence