dormouse (Member)
04-23-00 05:16
No 108758
      Indole-3-acetaldehyde sodium bisulfite addition compound -KrZ     

Author  Topic:   Indole-3-acetaldehyde sodium bisulfite addition compound 
Member   posted 07-17-99 08:57 PM          
Does anyone have any information on reacting this compound with dimethylamine? NaCNBH3 reduction perhaps? Any references would be appreciated (revdrone- cas search perhaps?). Seems as though I have access to this compound in my dreams.. Don't see why it wouldn't work in at least some yield... It says to store at 2-8C. Thanks.
Member   posted 07-23-99 02:29 PM          
Damn that shits expensive!! I think I'll go with indole-3-acetic acid. That certainly adds some difficulty to the procedure but it should still go pretty smoothly.. I'll be back with an update soon.
rev drone
Member   posted 07-27-99 12:03 PM          
Yep, if I were to go that route (which I wouldn't, when tryptamine is so cheap and plentiful, and the its aliphatic amine is a reasonably strong enough nucleophile for a fairly straight-forward Sn2 reaction), I'd codense indole acetic acid with dimethylamine using POCl3 or DCC, then reduce it with a strng reducing reagent like LAH (Gawd I hate doing LAH reductions.)
Still, this sodium bisulfite addition caught my attention, namely because I've done that same reaction with indole, and discovered over several grueling months that the preparative procedures in the literature, prior to a fantastic article written around 1990, we all full of crap. As you know, bisulfite acts as a very nice protecting group by reversibly adding across the 2,3 double bond, keeping harder-to-remove things from reacting there. Treat it with base, and the bisulfate comes off nicely, giving your the indole back.

In this case however, I think its overkill. There are plenty of cases where indole-based compounds of similar structure undergo reductions with stroner reducing reagents, and come out just fine. The reduction of beta-methyl-beta-nitrovinyl-3-indole to alpha methyl tryptamine comes to mind as a classic example.

Might I suggest paying a visit to DMT wolrd's chemistry forum? The subject has been hit pretty hard, and I think you'd enjoy it.

-the good reverend drone