The Hive > Tryptamine Chemistry

Fisher Tryptamine Synthesis - is this right?

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Rhodium:
Check out Patent US5607957, Patent US5510359 or Patent US5602162.

In the steps where they condense 4-chlorobutanal acetal with a phenylhydrazine, the product is directly the tryptamine - is that possible without an external amine source?

The atoms add up all right, but I couldn't imagine that the little ammonia split off from the hydrazine in the reaction would be enough to aminate the resulting 3-(2-chloroethyl)-indole...

dennis_pro:
Method of tryptamine producing via phenylhydrazine and gamma-chlorobutanal in EtOH is described in a russian book "Syntheses of getherocyclic compounds" at 1972. Ammonia is produced in a study of Fisher's rearrangement.
If you are interesting, I can translate the manual from russian and post it here ;) .
But it is more interesting to replace gamma-chlorobutanal with gamma-N,N-dimethylaminobutanal :)  in this synthesis.
With best regards,
Dennis Prochko aka Wolf

Rhodium:
It certainly is. I just find it sad that there are no easy route to form 4-chlorobutanal or its acetals... Most seem to require rosenmund reduction of the corresponding acid chloride, or alternatively requires the synthesis of 4-chlorobutanal (which easily reverts to THF), and then oxidizing this to the aldehyde.

Lilienthal:
UTFSE, there is one (unconfirmed) extremely simple published synth of it (I can't remember what it was, but I can search my papers if you can't find it here). And you can buy the (dimetyl-) aminobutyraldehyde acetal.

Rhodium:
You mean the one I found which used formic acid/NaHCO3/CHCl3? Yes, that's the problem - it hasn't been confirmed to work with this substrate in particular. And I don't remember if the starting material was the alcohol or the acid either.

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