anyone given though to this scheme?
 i don't see it anywhere in the literature.
 diazoltize tryptamine in the prescence of an acid like hcl to form the terminal haloethane substituted indol
after this one can easily make into det dipt etc by just substitution in alcohol with the appropriate amine.
get back to me on that?

the "N" you speak of is aromatic and does'nt  undergo the same reactions as an amine for instance.
diazotization conditions are mild around room temp i don't see problem

"The intermediates resulting from the diazotization of primary, aliphatic amines are unstable; they are rapidly converted into carbocations after loss of nitrogen, and yield products derived from substitution, elimination or rearrangement processes."

-- http://www.organic-chemistry.org/namedreactions/diazotisation.shtm

Unfortunately it won't work.

sorry been away but yes the sandemeyer reaction was what i was refeerring to.
 and instability i think that's kind of the idea of a diazonium salt, it's an intermediate.

Indoles that are unsubstituted in the 2 position, may be adversely effected under acidic conditions.

Diazotizations are usually performed on anilines. 

It is however, possible to Diazotize Amino Acids.  Theoretically, tryptophan could be  diazotized, the amino function displaced by a halogen, and the resulting Alpha-Halogen-acid...could be reacted with an N,N-alkyl-amine, to form an N,N-Di-alkyl-tryptophan.

Decarboxylation of course, might be difficult.  As the Di-alkylamino function is unable to form an imine.

Seems to be hard to actually isolate any aldehyde from this reaction.  No one I've heard of, has pulled it off. 

Might be possible to do it in-situ though, by reacting tryptophan with TCCA, thereby forming the indole-3-acetonitrile (and then reducing it).  Since the TCCA conditions are fairly mild, there is a reasonable chance of success at forming the acetonitrile.  Very high yields are routine for such reactions.
Need to confirm actual product?  Just hydrolyse some of your mystery material.  Lots of data on Indole-3-acetic acid.  Easy to identify.

Catalytic reduction of the nitrile, via hydrogenation, then proceeds via an unstable aldimine intermediate.  Indole-CH2CH=NH......Traditionally, in the hydrogenation of nitriles, the reduction solvent is saturated with ammonia to insure that only the primary amine forms.

However, if the reduction takes place in a solvent saturated with a secondary amine, say dimethylamine, replacement of the unstable primary aldimine by the N,N-Dimethyl-aldimine might become the favored reaction.  Resulting in the final reduction product being DMT.   An  analogous reduction is known to occur when Phenylacetonitrile is hydrogenated in the presence of Dimethylamine.

Nitriles from Aminoacids via TCCA.  SYNLETT. 2004, No.12, pp2180-2184

Buck Dimethylamino phenethylamine from phenylacetonitrile, hydrogenation
J.Am. Chem. Soc. 1938, 60  pp1789-1792


Might be better procedures, and I haven't actually seen this hydrogenation paper yet.  But folks claim it contains pertinent information.

Developing such a reaction sequence might result in a high yielding,  economical, and easy tryptamine synthesis.

Has he tried the  TCCA proceedure with other substrates? 

The author of Synlett TCCA procedure claims very high yields, but Tryptophan was not one of the materials he reported on.

The HNO₂ required can be synthesized without the need for NaNO₂.

HNO₂ + Sodium metabisulfite also forms HNO₂ insitu from the SO₂ formed from the bisulfite hydrolysis reducing the HNO₃ and testing of this has proved promising as an understatement.

Clean NaNO₂ is much harder to get then clean Nitric acid so say the least.

SO₂ is also a substitute to the Metabisulfite. Bubble SO₂ into concentrated HNO₃ then slowly under very cold condition drip this onto the amine you wish to undergo diazotation.