I tried with H2(g)/Pd on Carbon 10% wt at atmospheric pressure (balloon) but it did not work. Then I tried with ammonium formate and Pd/C at room temperature but it did not work either.
I was thinking to try with the shaker hydrogenator.
At which pressure should I work to be sure that the benzyl group will come out?
You can add 5-15%Pd(OH)2 and Pd/C mixture. This condition can debenzylation from amine very efficiently.
Good luck
Chinpiao Chen
Try at 3-5 bar in ethanol, if still not working try with Acetic acid or HCl present, there is some good information on hydrogenation chemistry in the link
http://jmcct.com/docs/handbook-pharmaceutical-catalysis.pdf
We have a paper in Chem. Pharm. Bull. 57(12) 1421—1424 (2009). You can see the detail procedure. If you can't get this paper, please contact me.
Chinpiao Chen
If Pd does not work, give a try to Pt, it will be "more powerfull". PtO2 would do the trick.
Dear
Simona Di Blasio
You may try also using Sn/Hcl. It my be useful.
10% Pd on carbon on H2 works very smoothly in 3 hrs to debenzylate the tertiary amine. You need more pressure of hydrogen in shaker hydrogenator. (use 50 psi in Parr apparatus).
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