Forgive me for I am not sober!!!
Was reading this : http://www.omsu.omskreg.ru/vestnik/articles/y1998-i1/a041/article.html# (http://www.omsu.omskreg.ru/vestnik/articles/y1998-i1/a041/article.html#)
and came up with an idea:
(not really related to the article)
1. prime amine is converted to pyridinium salt via reaction with 2,4,6-trimethyl-pyrillium (246TMP) clorate.
Example : tryptamine + 246TMP -> N-[2-(indol-3-yl)-ethyl]-2,4,6-trimethyl-pyridinium (Tryp246TMP)
Note: 2,4,6-pyridine is good leaving group, it seems.
2. Nucleophilic substitution with dialkyl amine.
Example: Tryp246TMP + [CH3NHCH2CH3]
__> N-methyl-N-Ethyl-Tryptamine
I guess, one can do "cold version" with corresponding
sodium dialkyl amide (e.g. Na[CH3NCH2CH3])
General Note: seems that it would be the best method
for convertening -NH2 into good leaving group in the case of indole derivatives;
oxidative methods, (e.g. -NH2 -> -N2+, etc.) usually mess
up pyrrol ring nitrogen as well, turning it into N-0 radical
Z_Hound
Any Possession is a Demonic Possession!