1: N-(3-methoxybenzylidene)cyclohexanamine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=-78 - -15°C; 1 h; 2: ethyl iodide in tetrahydrofuran; hexane T=20°C; 0.75 h;

1: 63 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -60 deg C to r.t. 2: 94 percent / 4 M aq. HCl / diethyl ether / 16 h / Ambient temperature View Scheme