piperidine in pyridine 1.) 80 deg C, 1 h, 2.) 100 deg C, 1 h, 3.) heating, 0.5 h;

platinum(IV) oxide; hydrogen P=2585.7 Torr;

1: 100 percent / hydrogen, Adam's catalyst / 2585.7 Torr 2: thionyl chloride / toluene / 3 h / 55 - 60 °C 3: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

(i) SOCl2, (ii) NaBH4, (iii) aq. HCl; Multistep reaction;