1: 82 percent / DCC / dimethylformamide / Ambient temperature 2: H2 / palladium 3: 53 percent / dimethylformamide / 4 °C 4: 79 percent / anisole, trifluoroacetic acid / 1 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

1: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.17 h 2: 4-(aminomethyl)piperidine / CHCl3 / 0.5 h 3: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.17 h 4: 4-(aminomethyl)piperidine / CHCl3 5: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.5 h 6: 4-(aminomethyl)piperidine / CHCl3 / 0.5 h 7: 1.) 95 percent TFA / 1.) 2 h, 2.) water, G-15 Sephadex View Scheme