Diisopropylethylamine → HCID 59850185, compound

Participants

Reaction Steps

4-Bromo-2,5-difluoronitrobenzene (0.60 g, 2.5 mmole) was dissolved in dry dimethylformamide (10 ml) and diisopropylethylamine (0.39 g, 3.0 mmole), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.53 g, 2.6 mmole) were added at room temperature and subsequently stirred for 1 hour. The mixture was then stirred at 80° C. for 2.5 h, then cooled to room temperature. The mixture was concentrated to dryness under vacuum and the residue partitioned between ethyl acetate and dilute aqueous potassium carbonate solution. The organic layer was dried over MgSO4, filtered and evaporated, and the residue was purified by silica gel chromatography eluting with 10 to 50% diethyl ether in 40-60 pet ether to afford the title compound as an orange/red solid, 0.91 g, 87%. LC/MS—97% m/e-416/418 (M−H).

Provenance & Evidence