N,N-dimethyl-aniline; trichlorophosphate 3 h; Heating;

1: 1.) HCl (gas), 2.) NaOEt / 1.) EtOH, 0-5 deg C, 24 h, 2.) EtOH, reflux, 2.5 h 2: 82 percent / NH4OH, NaOH, Raney Ni / H2O / 2 h / Heating 3: 47 percent / POCl3, N,N-dimethylaniline / 3 h / Heating View Scheme

1: 82 percent / NH4OH, NaOH, Raney Ni / H2O / 2 h / Heating 2: 47 percent / POCl3, N,N-dimethylaniline / 3 h / Heating View Scheme

1: 1.) NaH / 1.) CH3CN, 30 min, 2.) CH3CN, RT, overnight 2: 79 percent / NH3 / methanol / 16 h / 120 °C 3: 90 percent / H2, K2CO3 / 10percent Pd/C / H2O; propan-1-ol / 8 h / 1520 Torr View Scheme