lithium bromide in acetone 5 h; Heating;

1.1: NaH / benzene / 0.5 h / 20 °C 1.2: 92 percent / benzene / 1 h / 60 °C 2.1: 98.5 percent / hydrogen / Pd/C / ethanol / 2585.74 Torr 3.1: 100 percent / LiAlH4 / tetrahydrofuran / Heating 4.1: 77 percent / Et3N / CH2Cl2 / 16 h / 0 - 20 °C 5.1: 73 percent / LiBr / acetone / 5 h / Heating View Scheme

1: 98.5 percent / hydrogen / Pd/C / ethanol / 2585.74 Torr 2: 100 percent / LiAlH4 / tetrahydrofuran / Heating 3: 77 percent / Et3N / CH2Cl2 / 16 h / 0 - 20 °C 4: 73 percent / LiBr / acetone / 5 h / Heating View Scheme

piperidine; diphosphorus tetrabromide

1: 100 percent / LiAlH4 / tetrahydrofuran / Heating 2: 77 percent / Et3N / CH2Cl2 / 16 h / 0 - 20 °C 3: 73 percent / LiBr / acetone / 5 h / Heating View Scheme