1: 1) Na; 2) 10 percent HCl / 1.) 0 deg C, 16 h, 2.) MeOH, reflux 2: 55 percent / H2 / 10percent Pd/C / acetone / 24 h View Scheme

Multi-step reaction with 4 steps 1: 1) piperidine; 2) 0.25 N NaOEt / 1) 72 h, heating; 2) heating2: 70 percent / H2 / 10percent Pd/C / acetone3: 66 percent / K2CO3/NaI / acetone / 8 h / Heating4: 66 percent / K2CO3/NaI / acetone / 8 h / Heating  

Multi-step reaction with 3 steps 1: 70 percent / H2 / 10percent Pd/C / acetone2: 66 percent / K2CO3/NaI / acetone / 8 h / Heating3: 66 percent / K2CO3/NaI / acetone / 8 h / Heating  

Multi-step reaction with 2 steps 1: 66 percent / K2CO3/NaI / acetone / 8 h / Heating2: 66 percent / K2CO3/NaI / acetone / 8 h / Heating