Piperidine → 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide (Preparation 7(A)) (1.2 g, 2.7 mmol) and piperidine (0.4 mL, 1.33 mmol) in toluene was added 1H-indole-3-carbaldehyde (0.46 g, 3.2 mmol). The reaction mixture was heated at 110° C. for 31 hours. Activated 4 Å molecular sieves (2 g) were added. The reaction mixture was heated for 24 hours at 110° C. The reaction was cooled to room temperature and the molecular sieves were filtered with the aid of toluene. The filtrate was concentrated and the residue was purified by chromatography (12%-20% acetone/methylene chloride) to give 1.5 g of 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide as a solid. MS 579.2 (M+1).

Provenance & Evidence