piperidine in pyridine T=110°C; 5 h;

sodium acetate

1: phosphorus pentachloride; toluene / und Reduktion des erhaltenen sirupoesen 3,5-Dimethoxy-benzoesaeure-phenylimidchlorids mit Zinn(II)-chlorid und Chlorwasserstoff in Aether 2: sodium acetate View Scheme

alkali

1: H2 / 5percent Pd-C / ethyl acetate 2: 91 percent / polyphosphoric acid / 2 h / 70 °C View Scheme

hydrogen; palladium 10 on activated carbon in ethanol 16 h;

1: sulfuric acid 2: lithium aluminium tetrahydride; AlCl3, aluminium chloride 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone View Scheme

1: H2 / 5percent Pd-C / ethyl acetate 2: 91 percent / polyphosphoric acid / 2 h / 70 °C 3: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 4: 84 percent / n-butyl-lithium, diethylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 5: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene, -78 deg C, 2.5 h, 2.) room temperature, 30 min 6: 98 percent / m-hydrochloric acid / tetrahydrofuran / 12 h 7: 92 percent / aqueous potassium hydroxide / methanol / 24 h / 20 °C 8: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 9: 51 mg / H2 / 5percent Pd-C / ethyl acetate 10: 33 percent / sodium borohydride / methanol / 3 h View Scheme

1: H2 / 5percent Pd-C / ethyl acetate 2: 91 percent / polyphosphoric acid / 2 h / 70 °C 3: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 4: 98 percent / di-isobutylaluminium hydride / toluene View Scheme

1: H2 / 5percent Pd-C / ethyl acetate 2: 91 percent / polyphosphoric acid / 2 h / 70 °C 3: 96 percent / boron trichloride / CH2Cl2 / 2 h View Scheme