Stanley (Stranger)
08-06-01 22:40
No 201916
      Tryptamine from DL-tryptophane  Bookmark   

Greetings.

Recently, I gave the ketone-catalyzed decarboxylation of DL-tryptophan a try, and to my disappointment, the yield was somewhere around 2%. I speculate that the reason is the xylene used as solvent: its b.p. is 140 C. I figure this is not warm enough for a decarboxylation to take place (even if ketone-catalyzed).

I used 5 g of DL-tryptophan, 0,5 ml of MEK in 30 ml of xylene, and refluxed for 13 h (I thought the reaction time would compensate for the low temperature).

I'm thinking about trying the same ratio again, but I'll use naphtalene instead of xylene.

Comments?


Stanley
 
 
 
 
    foxy2
(Hive Addict)
08-06-01 23:50
No 201937
      Re: Tryptamine from DL-tryptophane  Bookmark   

You could also try a higher boiling keytone.

Thujone comes to mind as accessable one.
http://chemfinder.com  for the structure if interested
http://www.execpc.com/~goodscnt/data/es1040992.html


Do Your Part To Win The War
 
 
 
 
    Rhodium
(Chief Bee)
08-07-01 00:06
No 201941
      Re: Tryptamine from DL-tryptophane  Bookmark   

How was the tryptamine isolated? If the reaction did not produce more than 2% tryptamine, then you should be able to recover the rest of the tryptophan unchanged.

../rhodium
 
 
 
 
    Stanley
(Stranger)
08-07-01 00:44
No 201953
      Re: Tryptamine from DL-tryptophane  Bookmark   

I'm thinking cyclohexanone and naphtalene. The tryptamine was isolated as the hydrochloride salt. And yes, of course, the tryptophan is to be recovered!

I think I'll give that cyclohexanone/naptha a try, and see what I come up with.


Stanley
 
 
 
 
    foxy2
(Hive Addict)
08-07-01 12:55
No 202126
      Re: Tryptamine from DL-tryptophane  Bookmark   

Definately go for cyclohexanone.
My suggestion was for the less connected bee's.  You know that cyclohexanone is slightly watched right?  Due to its use in PCP.
Later
Foxy

Do Your Part To Win The War
 
 
 
 
    racemic
(Newbee)
10-13-01 07:35
No 223910
      Re: Tryptamine from DL-tryptophane  Bookmark   

If I don't get side tracked I'll be trying this reaction in d-limonene (bp 176) w/ ketone catalyst some time in the near future. d-Limonene is cheap and unwatched and seems to fit the requirements for this rxn. Any thoughts or comments?