okay, okay, okay. the question was stupid. had i looked in the merck index, i would have known that tryptamine is not soluble in chloroform and thus propbably neither in DCM.
but that leads me to new questions that puzzle me:
1) in Post 211603 (https://www.thevespiary.org/talk/index.php?topic=13266.msg21160300#msg21160300)
(Rhodium: "Another tryptophan decarboxylation", Tryptamine Chemistry):
A suspension of the L-Tryptophan copper chelate in DMSO was heated at 170-175°C for 10 minutes (until the evolution of carbon dioxide had ceased). After cooling, the resultant solution was filtered and to the filtrate was added a suitable amount of water. The reaction mixture was made basic with 30% sodium hydroxide solution and extracted with chloroform. After distillation of the solvent, the product was purified through column chromatography on silica gel, yield 40%. The tryptamine was identified as its hydrochloride salt, mp 246-248°C.
why are they extracting with chloroform?? tryptamine is not soluble in chloroform i thought! and it is not soluble in water either, so i would expect it to crash out of the solution when adding water. what's happening here??
2) in https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophan.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophan.html)
:
A good way to purify tryptamine without having to resort to distillation under strong vacuum is to dissolve the crude tryptamine hydrochloride in water, adjust the pH to between 7.6 and 8.2 and extract the solution with chloroform. The pH is then adjusted to 14 with NaOH and the pure tryptamine is filtered off with suction and air dried.
what is the purpose of this? is tryptamine at pH 7.6 - 8.2 still mainly the HCl salt? why extract with chloroform? tryptophan is only slightly sol in chloroform, isn't it?
in short: i dont get it. any help appreciated.