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Petroleum ether was added resulting in a huge emulsion.

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Pet ether is a very non-polar solvt and probably isn't very food for xtacting amines - i might bee wrong though.

You probably should try to use some other solvt, adjusting pH could help too, but you'll have a hard time figuring that unless you've got a pH meter.

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I wanted to saturate the aqueous layer with NaCl, but none was at hand so I added epsom salts (MgSO4.7H20)
The whole thing turned into a heavy sludge.

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Wrong! Always use NaCl. Probably unreacted tryptophane formed an insoluble w/Mg++ (By chance, you're certain it'a hydrate salt?)

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From the filtrate i separated the pet.ether, dried it and sat'd it with HCl gas, it turned red and a teenie weenie bit precipitated. Apparantly tryptamine base is not soluble in most organic solvents.

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Isn't tryptamine hcl soluble somewhat in non-polars? Well, not in pet. ether, i'd guess.

As for a way to purify it - recrystallize it, but ask someone else what solvent to use. A good thing would bee to know if it's really tryptamine - that is actually of a primary concern

And - please, follow my advice - always record all the weights and volumes in the course of your experiment - otherwise it becomes worthless for both the future generations and further optimization.

Looking forward to hear the sequel of your dream,

Antoncho

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This was mixed with DMSO in a RB flask with condensor and the resulting suspension heated at 175°C for 10 minutes. I was left with a darkbrown solution and a red precipitate which was assumed to be copper. It was allowed to cool to +-~50°C (it was still warm but i could hold the flask), and filtered.
Water was added to dilute the filtrate,
next, cold 10% NaOH solution was slowly added until pH=12

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i have heard a report about the same reaction and similar problems: 3gm of the copper chelate was decarboxylated in dmso. the darkbrown solution was filtered. water was added. and allready here lots of fine yellow precipitate formed. NaOH was added and the precipitate changed in consistency (much more clumpy and darker). after letting the precipitate settle for some hours, the liquid was decanted. the precipitate (which was now dark brown) was washed with NaOH solution (rationale: get rid of tryptophan and DMSO) and multiple times with water (rationale: get rid of NaOH) then dried on a 70°C hotplate. this gave a dark brown-black rocky powder. which dissolves very good in acetone and EtOH and nearly not at all in water, dcm and toluene.

so far all trys to isolate the HCl salt have failed. the reporter tried to acidify acetone and EtOH solutions with HCl, but only got really ugly black solutions. except once, when a spatula tip of the brown stuff was dissolved in 2ml acetone, a little water was added resulting in a bright yellow solution with black precipitate. the solution was decanted and 2 drops of conc HCl where added (to the solution) resulting in a bright yellow to white precipitate. unforunately all of it was lost in a blue ribbon filter and the reporter was never able to repeat this.

also dissolving in dcm, washing with Na(CO3)2 and water, then evaporating the dcm failed: result was always a dark red not pretty oil or black tar. gassing the dcm resulted in a little black powder.