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;

1: NBS, α,α'-azoisobutyronitrile / CCl4 / 2 h / Heating 2: Et3N, DMAP / CHCl3; CCl4 / 18 h / Ambient temperature View Scheme

1: 44 percent / HOBT, DCC / dimethylformamide / 18 h / Ambient temperature 2: 1.) POCl3, 2.) NaBH4 / 1.) 50 deg C, 3 h, 2.) DME, 20 deg C, 2.5 h View Scheme