1: (R)-(-)-1-phenyl-2-(piperidin-1-yl)ethanol With methanesulfonyl chloride; triethylamine in diethyl ether 0.5 h; 2: 1,3-diamino-propane With water; triethylamine in diethyl ether T=20°C; 16 h;

in isopropyl alcohol T=22°C;

1: piperidine; (R)-2-phenyloxirane in ethanol T=80°C; 5 h; 2: methanesulfonyl chloride With triethylamine in tert-butyl methyl ether T=-18 - -10°C; 3: 1,3-diamino-propane; Methanesulfonate(S)-1-phenyl-3-azonia-spiro[2.5]octane; in water T=20°C; 1 h;

1.1: ethanol / Heating 2.1: Et3N; MsCl / diethyl ether / 0.5 h 2.2: 67 percent / Et3N; H2O / diethyl ether / 16 h / 20 °C View Scheme

in diethyl ether; water 12 h; Ambient temperature; Yield given;

1.1: ethanol / Heating 2.1: Et3N; MsCl / diethyl ether / 0.5 h 2.2: 67 percent / Et3N; H2O / diethyl ether / 16 h / 20 °C View Scheme

1: triethylamine / diethyl ether / 30 h / Ambient temperature 2: H2O; diethyl ether / 12 h / Ambient temperature View Scheme