tert-butylamine in methanol 48 h; Ambient temperature;

1: 75 percent / LiAlH4 / tetrahydrofuran / 2 h / 5 °C 2: 95 percent / Et3N / CHCl3 / 1.) 0 deg C, 1 h, 2.) r.t., overnight 3: 95 percent / MnO2 / CHCl3 / 24 h / Ambient temperature 4: 95 percent / 2 N aq. HCl / ethanol / 15 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=5°C; 2 h;

tert-butylamine in methanol 48 h; Ambient temperature; Further byproducts given;

tert-butylamine in methanol 72 h; Ambient temperature;

1.1: tetrafluoroboric acid; sodium nitrite / water / 0.33 h / -15 - 0 °C 1.2: 3 h / Reflux 2.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C View Scheme

tert-butylamine in methanol 72 h; Ambient temperature;

1: 2-aminonaphthalene-3-carboxylic acid methyl ester With hydrogenchloride; sodium nitrite in water T=0°C; 1 h; 2: KSeCN With sodium acetate in water T=0 - 20°C;

1.1: sodium nitrite; hydrochloric acid / H2O / 1 h / 0 °C 1.2: 46 percent / sodium acetate / H2O / 0 - 20 °C 2.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 2.2: 93 percent / hydrochloric acid; air / diethyl ether 3.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 View Scheme

1.1: sodium nitrite; hydrochloric acid / H2O / 1 h / 0 °C 1.2: 46 percent / sodium acetate / H2O / 0 - 20 °C 2.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 2.2: 93 percent / hydrochloric acid; air / diethyl ether 3.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 4.1: 38 percent / potassium fluoride; calcium fluoride / various solvent(s) / 85 h / Heating View Scheme