Transamination idea

[n00dle]

Username:  Vitus_Verdegast
tryptamine + H2O <--Ni--> tryptophol + NH3
Dunno about this step, somehow I doubt its efficiency but if you could provide me with a ref, I'd be very happy to be proven wrong.

Can anyone find a reference? If not i can see a possible synth.. tryptophan + sugar --yeast--> tryptophol + ethanol.
The problem is the dimethylamine has such a low bp. what about a stainless steel bomb w/ dimethylamine, tryptophol and raney nick. in the oven? would the raney react with the vessle? if not, would the pressure affect the reaction? either way that might be the way to get around the DiMeAm-reflux-low boiling point problem.

[Herr_Ovalmeister]

Here's J.Chem.Soc.Perkin Trans.1, 8 (1984), p.1929-1932 in DejaVu format:

http://home.ripway.com/2003-12/43034/Chemtext1/jcstryp.djvu

[Herr_Ovalmeister]

DejaVu files don't seem to download from ripway.com.  Here's the article in pdf format.  Its over 900 KB so it might take a couple minutes to download.

http://home.ripway.com/2003-12/43034/Chemtext1/JCStrypA.pdf

[Herr_Ovalmeister]

Look at example 5 in column 7 here:

Patent US3450760

Only the worthy will understand its significance.

[Vitus_Verdegast]

Preparation of N,N-dimethylcyclohexylamine

N,N-dimethylcyclohexylamine was prepared using the apparatus of Example 1. Two parts of cyclohexylamine and 3 parts of dimethylamine were fed into the reactor tube along with 20 parts of hydrogen gas at a space velocity of 2000 and reacted at 200 p.s.i.g. at about 150-165°C. The crude product mixture contained 17.5% by weight of N,N-dimethylcyclohexylamine. Also present in the crude product mixture were 9.4% of N-methylcyclohexylamine and 16.3% of dicyclohexylamine. The remainder of the crude mixture was cyclohexylamine. The composition of the crude product mixture was determined by the vapor chromatography method.

Nice find, Sam!
Although the amount of pressure is not critical and it is only advantageous to increase the output of products and to facilitate fractional distillation of difficultly condensible components (page 4), what worries me a bit is the fact that these are vapor phase reactions, something which is not really practically feasible with tryptamine IMO. But this certainly doesn't mean that the idea of transamination is not viable.