1: POCl3 / Heating 2: PPA / Heating View Scheme

1: 1.) n-BuLi / 1.) THF, -40 deg C 2: POCl3 / Heating 3: PPA / Heating View Scheme

in tetrahydrofuran Reflux;

1: 4-chloro-1-methyl-piperidine With magnesium; ethylene dibromide in tetrahydrofuran T=20 - 48°C; 2: 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one in tetrahydrofuran T=-80 - -70°C; 2 - 3 h; Product distribution / selectivity;

1: tetrahydrofuran / Reflux 2: sulfuric acid / 4.5 h / 20 °C View Scheme

1: tetrahydrofuran / Reflux 2: sulfuric acid / 4.5 h / 20 °C 3: triethylamine / toluene / 3 h / Reflux View Scheme

1: tetrahydrofuran / Reflux 2: sulfuric acid / 4.5 h / 20 °C 3: triethylamine / toluene / 3 h / Reflux 4: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

1: 1) NBS, AIBN; 2) DBU / 1) CCl4, reflux, 1.25 h; 2) CH2Cl2, reflux, 1 h 2: 1) AgNO3, Br2; 2) DBU / 1) room temp., 8.5 h; 2) CH2Cl2, reflux, 2.33 h 3: 53 percent / tetrahydrofuran / 0.5 h / 0 °C 4: 1) 95percent aq. H2SO4, 2) CF3SO3H / 1) room temp., 40 min; 2) 1 h at room temp., then 2.5 h at 45-55 deg C, then 2.66 h at 60-70 deg C 5: 98 percent / Et3N / toluene / 0.42 h / 80 °C 6: 67 percent / 13percent aq. KOH / ethanol / 25 h / Heating 7: 89 percent / NaBH4 / methanol / 1.8 h / 0 °C View Scheme

1: 1) NBS, AIBN; 2) DBU / 1) CCl4, reflux, 1.25 h; 2) CH2Cl2, reflux, 1 h 2: 1) AgNO3, Br2; 2) DBU / 1) room temp., 8.5 h; 2) CH2Cl2, reflux, 2.33 h 3: 61 percent / tetrahydrofuran / 1 h / 0 °C 4: 1) 87percent aq. H2SO4; 2) CF3SO3H / 1) room temp., 30 min; 2) 115 deg C, 1 h 5: 84 percent / Et3N / toluene / 0.5 h / 80 °C 6: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 7: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme