11-20-03 23:57
No 472080
Well, actually, I lied. None of the papers here are exactly melatonin. But close enough to make some bees happy, I hope.
Just read the article on leuckart reaction with formaldehyde, thought maybee there's something there for bees to dimethylate with, w/out quaternization. But who knows? 5-meo-DMT is powerful, ne?
Ok, let's get to brass tacks.
JMC 2002, 4219. Benzocyloalkene derivatives as melatonin agonists. 2nd column, Method Q.
(R)-2,3-Dihydro-6-methoxy-1H-indene-1-et
(the molecule looks exactly like melatonin, except there's no indole nitrogen, and the second ring is saturated)
Under an argon atmosphere, a mixture of (R)-8c (1.0 g, 4.3 mmol) and hydrazine monohydrate (20 ml) was stirred under reflux for 24 h. To the reaction mixture was added brine, and the mixture was extracted with CHCl3. The extract was washed with brine, dried, and concentrated. The residue was diluted with EtOH (1ml), and 4 ml HCl/EtOH (1.5ml) was added. To the solution was added diethyl ether, and the solid that precipitated was collected by filtration. The crude solid was recrystallized from EtOH-ether to afford 0.78 g (80% yield).
Umm, what the hell? hydrazine? Ning doesn't know what to make of that one...never mind. Moving on...
JACS 1996, 9974. A proton-transfer probe of a polymer-water interface.
Sounds pretty unrelated to psychedelic chemistry doesn't it? Well read on, my dear bees, for this "probe" they speak of is nothing other than a napthalene derivative with an -Me-NH-Ac on one end, and a -O-Me on the other. I know, stretching it, but lets have a look-see, k?
6-(Aminomethyl)-2-methoxynapthalene.
A 2.29 g (10 mmol) portion of the above was mixed with 100 ml of Claisen's alkali (35.2 g of KOH and 25.2 ml of water diluted to 100 ml w/ MeOH). The mixture was refluxed for 18 h and allowed to cool to room temperature. After evaporation of solvent, the remaining oily white solid was filtered and washed several times with water to yield 1.81 g (9.7 mmol, 96% yield) of colorless crystals.
Could this bee the same "claisen" as the guy who did lignin digestion? Oh, wait, that's "Klason"...
...heh hehOK, here's one to tickle your feet with:
JMC 1982, 729. Tryptophan Analogues.
Col. 2, Method D.
Amino Acids. Method D.
A mixture of the N-acetylated amino ester (0.01 mol) and 13 ml of 10 N NaOH was refluxed 8 h. The mixture was cooled, diluted with 100 ml H2O, treated with Nuchar, and filtered. The filtrate was acidified to pH 5.5 with 6 N HCl, and the resulting mixture was diluted to 200 ml with H2O, treated with Nuchar, heated to boiling, and filtered while hot. The filtrate was evaporated in vacuo to dryness, and the residue was either crystallized or used directly for subsequent esterification.
This is N-acetylated 5-HTP ethyl ester molecule, which they convert to 5-HTP, basically, except the carboxylic acid group is one methyl off the chain.
Yield isn't stated, but is at min. 40%, based on the next step's input.
Finally, a really wierd one. I can't even imagine how to ascii draw it. Let's hope all the bees can read chem words better than this drone...
JMC 1994, 1196. Col 1, 5th compound.
2-(Aminomethyl)-4,5-bis(4-methoxyphenyl)
A mixture of 8b(the N-acetylated version)(6.43 g, 17.5 mmol) in 35% HCl (35 ml) was stirred at room temp. for 30 min, and then stirred and refluxed for 30 min. After cooling, the reaction mixture was poured into water. The resulting precipitate was collected by filtration and washed with water to afford 8c.HCl (5.48 g, 86.3%).
The way ning phrased its beilstein search was like this:
(MeO-Ph-GH5, GH-CH2-NH-Ac) ---> (MeO-Ph-GH5, GH-CH2-NH2)
Since according to ning's limited knowledge, the only parts of the molecule really relevant to the hydrolysis problem are the methyl ether on one side, and the acetamino group being sliced on the other.
It would appear that Na Dithionite, whatever that is, might not be necesary. Hope this helps.
Lead us for the Swarm!
