Piperazine → 1-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde

Participants

Reaction Steps

A mixture of 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (2.0 g, 7.83 mmol), piperazine (6.73 g, 78.3 mmol) and dioxane (25 mL) is heated at reflux overnight. After cooling to room temperature, water (100 mL) is added and after 1 hr the solids are collected by filtration, washed with water and purified by flash chromatography eluting with chloroform-5% methanol. Product containing fractions are combined and concentrated to afford 2-(piperazin-1-yl)-1-phenyl-1H-indol-3-carboxaldehyde (0.87 g, 36%) as a beige solid. A sample, mp 175° C., is purified by flash chromatography eluting with dichloromethane-5% methanol. NMR (CDCl3) 10.29 (1H, s), 8.27 (1H, d), 7.60 (2H, m), 7.51 (1H, t), 7.40 (2H, d), 7.23 (1H, m), 7.15 (1H, t), 6.98 (1H, d), 3.27 (4H, m), 2.78 (4H, m).

Provenance & Evidence