tryptamine--->triptyl halide--->goodies

[obia]

I've always wondered about this rxn..but now i'm retired i won't be able to try it 
tryptamine + tosyl chloride and base -> NN Di Tosyl tryptamine treat w/ halide ion in dmf or dmso to give tryptyl halide bromide probably easiest then treat with aqueous dimthylamine or whatever sec amine you have lying around the tertmnine will be produced in preference to the alcohol triptyl bromide is not hydrolysed by water at room temperature... it is probaly possible to to the reaction without producng the halide the ditosyl amine group is a pretty goood leaving group and can probably be replaced with a secondary amine of choice.
 references for the RNTs-->RX  quickly grabbed from March Advanced org chemistry..
helv chim acta 1980  63 2168
tetrahedron lett 1981 22 199

other alkylsulphonic acid chlorides or anhydrides can replace p-toluenesolphonyl chloride. Benzenesuplophonyl chloride for example

[Lilienthal]

I did a quick Beilstein search. You need strongly basic conditions for amino-ditosylation (NaH, conc. NaOH solution). Under these conditions I would expect indole-1-tosylation too. That would add an extra hydrolyzing step.

I found no indication that the ditosyl-amine amine is a leaving group at all (searching for -X, -NR₂, -NHR, -OH, and -OR products).

[obia]

NN DiTsamines are mentioned as leaving groups nucleophilic substitution with halide ion in dmf.  Advanced Organic Chemistry by jerry march 4th ed p436 and  on p355. March's organinc chemistry is seldom cutting edge and tends to stick with well documented reactions but it occasionally contains things that with a bit of lateral thought have promise..   This text refers to a paper by Miller and Thi in  helv chim acta 1980 63 2168 where there are further references.
I don't have access to helv chim acta,if some one who does would like to look up the paper mentioned above..better still scan and post it somewhere then I'm sure you'll find what the beilstein search failed to do. old fashioned literature search methods are best..but only if the journal is held by the library. hence the post 

In short I'll bet NN DiTs amines are leaving groups in an aliphatic amine to halide conversion, and this reaction has been used as an alternative to the pyriylium-pyridium salt method.
If someone wants to prove me wrong by pulling the paper then be my guest...the gauntlet is thrown down.