triethylamine in benzene

hydrogen; acetic acid; trifluoroacetic acid; palladium on activated charcoal in ethanol P=760 Torr; 12 h; Yield given;

1: 86 percent / 12 h / 160 °C 2: 1.) NBS, 2.) benzoyl peroxide / 1.) CCl4, 1 h, 2.) CCl4, 60 deg C, 24 h 3: sodium azide / dimethylformamide; H2O / 12 h / 140 °C 4: H2, acetic acid, trifluoroacetic acid / 10percent Pd/C / ethanol / 12 h / 760 Torr View Scheme

1: 1.) NBS, 2.) benzoyl peroxide / 1.) CCl4, 1 h, 2.) CCl4, 60 deg C, 24 h 2: sodium azide / dimethylformamide; H2O / 12 h / 140 °C 3: H2, acetic acid, trifluoroacetic acid / 10percent Pd/C / ethanol / 12 h / 760 Torr View Scheme