Z_Hound
(Stranger) 03-31-02 12:42 No 290447 |
Methylation: Eschweiler-Clark | Bookmark | ||||||
In this reductive methylation method formic acid serves as a reductunt; anyone else trying it with tryptamine? See: [1] Moore, M.L. Org. React., 1949, 5, 301 [2] J.C.S., 1342 (1950) [3] J. Org. Chem., 50, 1110 (1985) [4] J. Org. Chem., 51, 5169 (1986) [5] Joseph Casanova and Praveena Devi, Synth. Comm., 23(2), 245-251 (1993) Procedure below is taken from ref. [5]: 5 mmol of prime amine is dissolved in minimal amount of ether and placed in a 3-neck rbf equipped with a reflux condenser and a magnetic stirrer. Solution is cooled to 0 C followed by addition of formaldehyde (38%, 9 mL) and formic acid ( 85%, 10 mL) (Authors in [5] report that reaction is exotermic upon addition of formic acid, in the case tryptamine it was not that obvious to me.) After the addition the mix is heated at 80 C for 10 hrs Cooled to RT Ether was added (50 mL), mix was neutralized with 20% NaOH and stirred for 10 min. Extracted with ether, -combined organic layers were dried over MgSO4. and the solvents removed. ------------ DO IT NOW! Z_Hound Any Possession is a Demonic Possession! |
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Z_Hound (Stranger) 03-31-02 12:53 No 290448 |
damn these carbolines | Bookmark | ||||||
Well, seems it is good with synthesis of betacarboline at least. Still, the residue after evaporation, far from pure on TLC (I suspect mixture of dmt and carboline, and may be some 2- methyl); gave sweet 1-hr mild trip with break through into Plato realms, when bioassayed (vapor) also, I believe, 2-Methyl substitute was present How would I avoid formation of carbolines? I ll do low tempr, and reduce time. Z_Hound Any Possession is a Demonic Possession! |
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Lilienthal (Moderator) 03-31-02 13:18 No 290453 |
beta-Carboline formation can't be avoided | Bookmark | ||||||
Unfortunately it's impossible. beta-Carboline formation can't be avoided under acidic conditions. |
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Z_Hound 03-31-02 13:33 |
should be ok with 2-sdbstitutes
(Rated as: insignificant) |
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PolytheneSam (Master Searcher) 03-31-02 14:18 No 290475 |
beta-Carboline | Bookmark | ||||||
There's a lot of hits for beta-Carboline when UingTFSE. http://www.geocities.com/dritte123/PSPF. The hardest thing to explain is the obvious |
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Z_Hound 03-31-02 15:03 |
yeah, those damn carbolines are everywhere!
(Rated as: insignificant) |
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foxy2 (Distinctive Doe) 04-01-02 00:11 No 290767 |
active? | Bookmark | ||||||
Are tryptamines with a saturated indole ring double bond active? Those who give up essential liberties for temporary safety deserve neither liberty nor safety |
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cilliersb (Hive Bee) 04-01-02 03:23 No 290835 |
Just a shot in the dark | Bookmark | ||||||
How about boiling your final product in Ethanolamine. Might just do the trick?? |
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Lilienthal (Moderator) 04-01-02 07:53 No 290916 |
Foxy: As far as it is known they are inactive. | Bookmark | ||||||
Foxy: As far as it is known they are inactive. cilliersb: Ethanolamine - huh?! No way... |
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PolytheneSam (Master Searcher) 04-01-02 19:03 No 291201 |
reference | Bookmark | ||||||
Note reference here Post 276458 (PolytheneSam: "Benzothiophene analogs", Tryptamine Chemistry) http://www.geocities.com/dritte123/PSPF. The hardest thing to explain is the obvious |
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obia (Stranger) 04-04-02 04:23 No 292287 |
i guess one way to use formic acid/ formaldehyde ... | Bookmark | ||||||
i guess one way to use formic acid/ formaldehyde is to reduce the indol double bond first with cat h2. do the methylation, then oxidise with Mno2. the reduction of tryptophan to dihydrotryptophan is used in on of the lysergic acid synths. |
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