1: sulfuric acid / 4.5 h / 20 °C 2: triethylamine / toluene / 3 h / Reflux 3: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

sodium hydroxide; tetrabutylammomium bromide in dichloromethane; water T=0 - 20°C; 13 h; Product distribution / selectivity;

4-(N,N-dimethlyamino)pyridine; triethylamine in tetrachloromethane; chloroform 18 h; Ambient temperature; Yield given;

1: 3,5-dimethyl pyridine With N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane T=75 - 80°C; 1.5 h; 2: 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-ylidene)piperidine With 4-(N,N-dimethlyamino)pyridine; triethylamine in tetrachloromethane; chloroform T=25 - 30°C; 18 h; 3: With sodium hydrogencarbonate in tetrachloromethane; chloroform; water 0.25 h; Product distribution / selectivity;

pyridine in dichloromethane

acetic acid T=20°C; 2 h;