Potassium Carbonate → HCID 131729335, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-2-nitroaniline (8.60 g, 50 mmol, commercially available from Aldrich), 1-tert-butoxycarbonyl piperazine (14.0 g, 75 mmol, commercially available from Aldrich)), anhydrous potassium carbonate (6.9 g, 50 mmol) and DMA (60 mL) were combined in a thick walled pressure fitted with a Teflon stirrer bar and sealed with a Teflon screw-top stopper. The reaction mixture was heated to 144° C. with stirring for 24 hours. The reaction mixture was allowed to cool to room temperature, filtered and the recovered solid washed with ethyl acetate. The filtrate was partitioned between water and ethyl acetate, and the organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude material was purified by silica chromatography eluting with 25% ethyl acetate-hexane which gave 11.8 g of tent-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate (80% yield). 1H-NMR (400 MHz, MeOH-d4): 7.95 (d, 1H), 6.37 (dd, 1H), 6.18 (d, 1H), 3.53 (s, 4H) 3.35 (s, 4H), 1.43 (s, 9H). MS (EI): 323 (MH+).

Provenance & Evidence