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


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.


(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.  for the structure if interested

Do Your Part To Win The War
(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.

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.

(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.

Do Your Part To Win The War
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?