hydrogen; palladium on activated charcoal in methanol P=1551.4 Torr; 0.75 h;

1: Et3N / toluene / Heating 2: cyclohexene / Pd/C / ethanol; tetrahydrofuran / Heating View Scheme

1: 65 percent / hydrogen chloride / 24 h / Heating 2: 68 percent / 1.) hydroxylamine, KOH, 2.) 12 percent HCl / ethanol; methanol / 1.) a) 0-4 deg C, 6 h, b) RT, 48 h 3: 70 percent / H2 / 10 percent Pd/C / methanol / 0.75 h / 1551.4 Torr View Scheme

1: 68 percent / 1.) hydroxylamine, KOH, 2.) 12 percent HCl / ethanol; methanol / 1.) a) 0-4 deg C, 6 h, b) RT, 48 h 2: 70 percent / H2 / 10 percent Pd/C / methanol / 0.75 h / 1551.4 Torr View Scheme