1: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr 2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature 3: 92 percent / 1N NaOH / ethanol / 4 h / 60 °C View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal T=50°C; P=3750.3 Torr; 10 h; Yield givenYields of byproduct given. Title compound not separated from byproducts;

1: H2, aq. HCl / 10 percent Pd/C / 10 h / 50 °C / 3750.3 Torr 2: 29 percent / PPh3, Et3N, CCl4 / acetonitrile / 15 h / Ambient temperature View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 &deg;C<br />2: tetrahydrofuran; toluene / 3 h / Heating<br />3: 4N aq. HCl / toluene; tetrahydrofuran / 20 &deg;C<br />4: Et₃N, TiCl₄ / toluene / Ambient temperature<br />5: 66 percent / H₂, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 &deg;C / 150012 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 &deg;C<br />2: tetrahydrofuran; toluene / 3 h / Heating<br />3: 4N aq. HCl / toluene; tetrahydrofuran / 20 &deg;C<br />4: Et₃N, TiCl₄ / toluene / Ambient temperature<br />5: 66 percent / H₂, Ti(O-iPr)4 / Raney-Ni / ethanol / 160 h / 160 &deg;C / 150012 Torr<br /> <br /> &nbsp;