Lem2 (Stranger)
05-12-01 18:47
No 193908
      Urushibara Catalyst for DIPT  Bookmark   

Ok, if you started out w/ tryptamine in a resonably pure form, would an STP Urushibara Catalyst reaction be an adequate reducing environment to run something like a TIHKAL #47 'cept w/ twice the acetone?

TIHKAL #47:
"The crude N-methyltryptamine obtained above (which can be substituted with 1.20 g of pure NMT) was dissolved in 50 mL ethanol, treated with 1.0 mL acetone, then with 0.5 g 10% Pd/C, and the reaction mixture shaken under a hydrogen atmosphere at 50 psi for 15 h. The catalyst was removed by filtration through a bed of Celite, the filtrate was stripped of solvent under vacuum, and the solid residue recrystallized from Et2O/hexane to give 0.93 g N-methyl-N-isopropyltryptamine (MIPT) which had a mp 82-83 C. Fom the benzyloxycarbonyltryptamine, yield was 56%. From NMT the yield was 62% of theory. Anal: C14H20N2. C,H,N. MS (in m/z): C5H12N+ 86 (100%); indolemethylene+ 130 (10%); parent ion 216 (2%). Efforts to isopropylate NMT with an excess of isopropyl iodide in isopropanol gave a 51% yield of a distilled product that did not crystallize."
 
 
 
 
    Rhodium
(Chief Bee)
05-13-01 05:42
No 194011
      Re: Urushibara Catalyst for DIPT  Bookmark   

At first (from tryptamine and acetone) N-isopropyltryptamine would form. I think that molecule is too sterically hindered to adequately form the imine with another molecule of acetone and be reduced by H2 (at least in good yields). I hope you can prove me wrong.


http://rhodium.lycaeum.org
 
 
 
 
    Lem2
(Stranger)
05-13-01 14:04
No 194098
      Re: Urushibara Catalyst for DIPT  Bookmark   

Do you think elevated pressures would help w/ that? I kinda wanted to stay away from pressurized reactions, but I think I could rig something up if needed. hmm... how pH sensitive is Tryptamine? Maybe you could get the Urushibara catalyst ready as usuall, but place enough HCL/Al foil in it at the same time to create the theoretical amount of hydrogen. Then you could seal it up really quickly in a pipe bomb of some sort. Prolly no a good idea w/ larger quantity's but, a little explosion never hurt anyone! tongue