illustrated history of my indol-3-yl N,N-diethylglyoxylamide

jory · Mon May 09, 2005 2:41 am

my friend (but i dont know him) like to cook, and mix 10g indole in 150ml dry et2o:

next, he start dropping 7,5ml oxalyl chloride in 50ml dry ether to this indole:

after 7 min. he get very nice crystals of indol-3-ylglyoxyl chloride (all good tryptamine-bears like this!):

NExt (about add all chloride) he mix it about 30min and after this he wash it with ether.

Next he add 20ml dry diethylamine in 40ml of ether to this mixture, yellow go to off-white and it look like diethylamide:

After wash with 2n hcl diethylamide look like that. upper layer is product with ether:

He filtrate it and get dirty product (red dots is unreacted chloride):

He dont like dirt and he wash it with water:

...
filtrate and dissolve in about 250ml of methanol. he like ice-cream and he get it!

ice-cream?:

after drying he get ~15g of product:

evaporate of 100ml of methanol and crystalize can get about 0,5g of product.

nice? very nice! Very Happy

brain · Linguist Extraordinaire

its wery nice !! Very Happy

-did you dry your ether? ower Na-metal destillation? or did uoy use boughted ethyl ether?? Smile

jory · Tue May 10, 2005 1:19 pm

brain · Linguist Extraordinaire

what you will do next with that? Smile

LAH ?

jory · Tue May 10, 2005 11:31 pm

brain · Linguist Extraordinaire

heh....

sory, i forgot who made that substance - your friend Wink

...

-what he will do with it? do you know? Smile

-Can it be transformed to DET only using LAH ? how your friend will do that? I'm especialy warried about inert atmospher Smile

jory · Wed May 11, 2005 12:28 am

IndoleAmine · Dreamreader Deluxe

Water = boom, make sure to use LAH on good weather days only, also dry your solvent thoroughly (silica gel or molecular sieves work very well IME)..

Inert atmosphere isn't needed, a drying tube can be advantageous..

jory · Wed May 11, 2005 9:19 pm

mk-1 · Wed May 18, 2005 3:25 am

Anyone knows if indol-3-yl N,N-dialkylglyoxylamide can be reduced with other reducing agents then LAH? swim dont like working with LAH

brain · Linguist Extraordinaire

i dont like working with alh-to Smile

but i dont thin Al/Hg will be good here, mabey nabh4? i dont think it will be good to? Smile

mk-1 · Wed May 18, 2005 5:53 pm

Well, since NaBH4 is a non selective reducer (meaning it is the opposite from an oxidizer), i think it might to the trick, but probably molar excess would be neede, if possible. Maybe anothr borohydride of a different metal, whos free ion has more then +1 charge, ie Zinc borohydride, Calcium borohydride.
I will dig more.

Seems like amides can be reduced to amines with NaBH4 see
Some Observations on the Preparation of Amides and their Reduction to Amines in Ionic Liquids.
Lampariello, Lucia R.1; Peruzzi, Daniela 1; Sega, Alessandro 1; Taddei, Maurizio 1
Letters in Organic Chemistry, May 2005, vol. 2, no. 3, pp. 265-270(6)
Bentham Science Publishers

I will search for more info
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mk-1 · Wed May 18, 2005 6:37 pm

Also, maybe it is possible to use the reducing agent NaBH4 or LiBH4 in the presence of Chlorotrimethylsilane as in the reducing procedure outlined in Angew. Chem. Int. Ed. Engl. Vol 28, No. 2, 218-220 (1989) (also visible in rhodium mirror)

And one last note for today, probably red-al would be as good as LAH. not 100% sure though. experimentation is needed...

transistor child · gnome

Boranetetrahydrofuran-complex will reduce amides to amines.
See http://www.basf.com/inorganics/pdfs/bulletins/BTHF.pdf

Would be real nice to have som first hand experiences with DMT and this reducing agent. Looks promising.