hydrogenchloride; water in acetonitrile 0.75 h; Reflux;

hydrogenchloride; thiourea in sulfolane

hydrogenchloride; acetic acid T=70 - 80°C; debenzylation;

1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h 2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

1: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 2: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 3: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 4: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 5: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 6: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

1: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 2: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 3: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 4: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

1: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 2: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 3: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

1: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 2: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 3: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 4: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 5: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

in methanol; palladium

1: imidazole / dimethylformamide 2: LAH / 3 h / 20 °C 3: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C 4: AcOH; piperidine / toluene / 4 h / Heating 5: HCl / methanol / 0.25 h 6: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme