4-(Piperidin-1-ylmethyl)aniline → 6-bromo-4-[[4-(piperidin-1-ylmethyl)anilino]methylidene]isoquinoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (100 mg, 0.350 mmol) and 4-piperidin-1-ylmethyl-phenylamine (67 mg, 0.35 mmol) are suspended in 5 ml of dimethylformamide. Mixture is heated at 115° C. for 2 hours forming a homogeneous mixture. Mixture is cooled to room temperature and concentrated on high vacuum to yield an orange oil. Residue is taken up in ethyl ether causing an orange solid to form. Mixture is filtered, and residue washed with 50 ml of ethyl ether to afford the product as an orange solid (130 mg, 0.296 mmol, 85%); 1H NMR (DMSO-d6) δ 1.37-1.52 (m, 6H), 2.25-2.36 (m, 4H), 3.40 (s, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.39 (dd, J=1.6, 8.4 Hz, 1H), 7.52 (d, J=8.5 Hz, 2H), 7.89 (d, J=8.4 Hz, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.92 (d, J=12.8 Hz, 1H), 11.39 (s, 1H), 12.50 (d, J=12.7 Hz, 1H).

Provenance & Evidence