hydrogenchloride; hydrogen; palladium on activated charcoal in isopropyl alcohol P=2585.7 Torr; 96 h;

1: pyridine / 48 h / Ambient temperature 2: 1.) NaH / 1.) N,N-dimethylformamide, room temperature, 24 h, 2.) N,N-dimethylformamide, 50 deg C, 7 days 3: 80 percent / H2, conc. HCl / 10percent Pd/C / propan-2-ol / 96 h / 2585.7 Torr View Scheme

1: 1.) NaH / 1.) N,N-dimethylformamide, room temperature, 24 h, 2.) N,N-dimethylformamide, 50 deg C, 7 days 2: 80 percent / H2, conc. HCl / 10percent Pd/C / propan-2-ol / 96 h / 2585.7 Torr View Scheme

1: 1.) NaH / 1.) N,N-dimethylformamide, room temperature, 24 h, 2.) N,N-dimethylformamide, 50 deg C, 7 days 2: 80 percent / H2, conc. HCl / 10percent Pd/C / propan-2-ol / 96 h / 2585.7 Torr View Scheme

hydrogenchloride in methanol 12 h; Ambient temperature;

1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Ambient temperature 2: hydrogen / palladium on carbon / ethanol 3: pyridine / 48 h / Ambient temperature 4: N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride / 1.) DMF, RT, 24 h, 2.) DMF, 50 deg C, 7 d 5: hydrogenchloride / methanol / 12 h / Ambient temperature View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C 2: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Ambient temperature 3: hydrogen / palladium on carbon / ethanol 4: pyridine / 48 h / Ambient temperature 5: N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride / 1.) DMF, RT, 24 h, 2.) DMF, 50 deg C, 7 d 6: hydrogenchloride / methanol / 12 h / Ambient temperature View Scheme

1: sodium hydride; p-toluenesulfonyl chloride / tetrahydrofuran / 4 h / Ambient temperature 2: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C 3: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Ambient temperature 4: hydrogen / palladium on carbon / ethanol 5: pyridine / 48 h / Ambient temperature 6: N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride / 1.) DMF, RT, 24 h, 2.) DMF, 50 deg C, 7 d 7: hydrogenchloride / methanol / 12 h / Ambient temperature View Scheme

1: sodium hydride / 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 2 h 2: trifluoroacetic acid / 48 h / 50 °C 3: sodium hydride; p-toluenesulfonyl chloride / tetrahydrofuran / 4 h / Ambient temperature 4: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C 5: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Ambient temperature 6: hydrogen / palladium on carbon / ethanol 7: pyridine / 48 h / Ambient temperature 8: N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride / 1.) DMF, RT, 24 h, 2.) DMF, 50 deg C, 7 d 9: hydrogenchloride / methanol / 12 h / Ambient temperature View Scheme

1: hydrogen / palladium on carbon / ethanol 2: pyridine / 48 h / Ambient temperature 3: N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride / 1.) DMF, RT, 24 h, 2.) DMF, 50 deg C, 7 d 4: hydrogenchloride / methanol / 12 h / Ambient temperature View Scheme