1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere 2: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 3: pyridine / 16 h / 20 °C 4: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 5: sodium tetrahydroborate / methanol / 3 h / 20 °C 6: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 7: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 8: lithium aluminium tetrahydride / 5 °C / |Reflux 9: 5 palladium on charcoal; hydrogen / methanol / 16 h 10: CHIRALPAK AD-H column / |Resolution of racemate 11: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 12: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C 13: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C View Scheme

potassium carbonate in acetone 2.5 h; Heating; Yield given;

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere 2: hydroxylamine hydrochloride; pyridine / 16 h / 120 °C 3: pyridine / 16 h / 20 °C 4: potassium ethanolate / ethanol; benzene / 5 h / 0 °C / |Inert atmosphere 5: sodium tetrahydroborate / methanol / 3 h / 20 °C 6: sodium hydroxide / dichloromethane / 3 h / 0 - 20 °C 7: sodium hydride / tetrahydrofuran; acetonitrile; mineral oil 8: lithium aluminium tetrahydride / 5 °C / |Reflux 9: 5 palladium on charcoal; hydrogen / methanol / 16 h 10: CHIRALPAK AD-H column / |Resolution of racemate 11: 1H-imidazole / dichloromethane / 16 h / 0 - 5 °C 12: pyridine / 3 h / 0 - 25 °C View Scheme

1.1: 4-hydroxy-benzoic acid; benzylamine / toluene / 6 h / 108 - 110 °C 2.1: ammonia; hydrogen / methanol / 40 - 45 °C / 0.38 Torr / |Autoclave 3.1: hydrogenchloride / ethyl acetate; isopropyl alcohol; hexane / 0.5 h / 0 - 15 °C / pH < 2 4.1: sulfur / 185 - 190 °C 5.1: sodium acetate / methanol / 65 - 68 °C 5.2: |Reflux 6.1: potassium carbonate / acetone / 5 h / |Reflux View Scheme

1: 4-hydroxy-benzoic acid; benzylamine / toluene / 6 h / 108 - 110 °C 2: palladium on activated charcoal / toluene / 30 h / |Reflux 3: potassium carbonate / acetone / 3 h / |Reflux View Scheme

potassium carbonate in N,N-dimethyl-formamide T=20°C; 18 h;

potassium carbonate in N,N-dimethyl-formamide T=80 - 100°C; 4 h;

in N,N-dimethyl-formamide

1: 97 percent / 2,6-dimethylpyridine, 4-N,N-dimethylaminopyridine / CH2Cl2 / 2 h / Ambient temperature 2: 90 percent / triethylamine / palladium(II)acetate, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 2 h / 70 °C View Scheme

1.1: 4-hydroxy-benzoic acid; benzylamine / toluene / 6 h / 108 - 110 °C 2.1: ammonia; hydrogen / methanol / 40 - 45 °C / 0.38 Torr / |Autoclave 3.1: hydrogenchloride / ethyl acetate; isopropyl alcohol; hexane / 0.5 h / 0 - 15 °C / pH < 2 4.1: sulfur / 185 - 190 °C 5.1: sodium acetate / methanol / 65 - 68 °C 5.2: |Reflux View Scheme