sodium hydroxide in water

Multistep reaction;

1: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.5 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 / 0.5 h 5: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.17 h 6: 4-(aminomethyl)piperidine / CHCl3 7: benzotriazolyloxy-tris(pyrrolidino)-phosphonium hexafluorophosphate, diisopropylethylamine / CHCl3 / 0.5 h 8: 4-(aminomethyl)piperidine / CHCl3 / 0.5 h 9: 1.) 95 percent TFA / 1.) 2 h, 2.) water, G-15 Sephadex View Scheme

With  triethylamine; dicyclohexyl-carbodiimide in  dichloromethane; N,N-dimethyl-formamide  1.) -20 deg C, overnight, 2.) RT, 4 h;