1: N-methyl-N-phenyl-N-(2-hydroxyethyl)amine With sodium hydride in tetrahydrofuran; mineral oil T=0°C; Inert atmosphere; 2: methyl iodide in tetrahydrofuran; mineral oil T=0 - 20°C; Inert atmosphere;

1: N-methyl-N-phenyl-N-(2-hydroxyethyl)amine With sodium hydride in tetrahydrofuran T=20°C; deprotonation; 1 h; 2: dimethyl sulfate in tetrahydrofuran T=20°C; Methylation;

sodium hydride in tetrahydrofuran T=20°C; Methylation;

1.1: 72 percent / NaHCO3 / methanol / 90 h / 20 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 84 percent / tetrahydrofuran / 20 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 2.2: 19 h / 0 - 20 °C View Scheme

1.1: sodium carbonate / ethanol / 15 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 3.2: 19 h / 0 - 20 °C View Scheme

toluene