Author Topic: tryptophol reduction question  (Read 1600 times)

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n00dle

  • Guest
tryptophol reduction question
« on: July 02, 2004, 05:06:00 AM »
Hey,
this page

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophol.html

talks about dialkyltryptamines from tryptophol. Now obviously this is a reducive amination style reaction, that reduces the tryptophol to it's aldehyde, so why does it only mention dialkyltryptamines? shouldnt it be viable with any amine, such as monoalkylamines and trialkylamines? i dont see why this synth is limited to DXT [where x is methyl, ethyl, etc.] when it could obviously be used for DPT, DIPT, and other interesting things, if one had the right legal situations.
Or does this method have something special about it that prevents this from happening?

Rhodium

  • Guest
why only secondary amines are suitable
« Reply #1 on: July 02, 2004, 03:20:00 PM »
shouldnt it be viable with any amine, such as monoalkylamines and trialkylamines?

Trialkylamines are unable to add to aldehydes as they are already fully substituted. Monoalkylamines may work to some degree, but will likely give lots of dimeric byproducts as two aldehydes are able to add to it (after the first aldehyde has added, the product itself is a secondary amine).