Piperidine → 2-Benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of piperidine (0.40 g, 4.7 mmol) in 5 mL of DMF was added a mixture of 2-benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione (A) and 2-benzyloxy-5-bromo-7-nitro-benzo[de]isoquinoline-1,3-dione (B) (0.50 g, 1.2 mmol, from Example S1-A,B). The reaction was heated to 120° C. for 4 hours, cooled, and the solvent removed under vacuum. The residue was chromatographed using chloroform/ethyl acetate (10:1) to give a mixture of the title compounds which were separated by crystallization from chloroform/hexane/ethyl acetate (5:5:1) to give 0.27 g of 2-benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (A) and 0.10 g of 2-benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (B).

Provenance & Evidence