This guy said he will explain to you two elseware how he knows what is in the system. The precursor was an amine. The product is an amine and the possible side reactions are... you guessed it... Amine.

The only possible side product is in itself an amine only with a fully reduced benzene ring attached, get it.

The scientific paper I read all this in said that with the addition of IpOH and another evaporation on a warm/hot water bath the Heptane oil can be seen leaving the system asa ever thinning oil film on the surface. The smell of Gassoline was smell before anyone even made mention if it so I hear. This was never smelled until they added IpOH for the second evaporation.

And Naf.... as far as the fumes comming off your HCl bottle. Thats does nojutice. Open it next to an open bottle of husehold ammonia if you want to understand what is being seen by these scientist.

I thing that the chlorination/bromination won't be a big problem, there are several recipes and several reagents for this with really good yields.

The reaction with NaOMe is also not a problem...

The ethylation and the separation of the different compounds... That's a problem....

Well the procedure given that you said is no problem gets you to syringaldehyde (4-Hydroxy-3,5-dimethoxybenzaldehyde), the next step should not be that hard here is an example (one of a few different ways) of how Shulgin went about it in Pihkal;

"3C-E: 3,5-Dimethoxy-4-ethoxyamphetamine

SYNTHESIS: A solution of 3.6?g syringaldehyde (3,5-dimethoxy-4- hydroxybenzaldehyde) in 50?mL MeOH was combined with a solution of 3.7?g 85% KOH in 75?mL warm MeOH. This clear solution suddenly set up to crystals of the potassium salt, too thick to stir satisfactorily. To this suspension there was added 7.4?g ethyl iodide (a large excess) and the mixture was held at reflux temperature with a heating mantle. The solids eventually loosened and redissolved, giving a clear amber-colored smooth-boiling solution. Refluxing was maintained for 2 days, then all volatiles were removed under vacuum. The residue was dissolved in 400?mL H2O, made strongly basic with 25% NaOH, and extracted with 4×100?mL CH2Cl2. The pooled extracts were washed with saturated brine, and the solvent removed under vacuum to give 3.3?g of a pale amber oil which set up as crystals of 3,5-dimethoxy-4-ethoxybenzaldehyde with a mp of 47–48?°C. A small sample recrystallized from methanol had a mp of 48–49?°C

From Pihkal
http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=25

note; Easy work up and you can recrystallize from methanol!

If diethyl oxalate works, which I assume it does, I'd much rather work with it than with an ethyl halide!

Good looking Enk, but Diethyl Carbonate is the sure bet in this case!

Dimethyl carbonate and phenols to alkyl aryl ethers via clean synthesis
Samedy Ouk,a Sophie Thiébaud,*a Elisabeth Borredona and Pierre Le Garsb
Green Chemistry, 2002, 4, 431–435

The industrially important alkyl aryl ethers (ArOR) were selectively obtained in good yields from the O-alkylation
of the corresponding phenols with the environmentally benign reagents, dimethyl carbonate or diethyl carbonate.
The reactions were carried out under atmospheric pressure, in a homogenous process, without solvent and in the
presence of potassium carbonate as catalyst.

http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b203353b&JournalCode=GC

93% yield for Eugenol!

Preparation of aralkyl phenyl ethers and alkyl phenyl ethers
United States Patent 4192949

Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.

EXAMPLE 5

33 parts of eugenol, 50 parts of dimethyl carbonate and 0.5 part of p-dimethylaminopyridine are kept for 20 hours at 200° C. Working up takes place as described in Example 1. 28 parts (99% of theory, based on converted starting material II) of eugenol monomethyl ether of boiling point 69°-70° C./0.13 mbar are obtained. The conversion is 80 percent.

EXAMPLE 25

33 parts of eugenol, 50 parts of dimethyl carbonate and 2 parts of tri-n-butylphosphine are kept for 15 hours at 190° C. Working up takes place as described in Example 24. 31 parts (88% of theory, based on converted eugenol) of eugenol methyl ether of boiling point 69°-70° C./0.13 mbar are obtained. The conversion is virtually quantitative.

http://www.freepatentsonline.com/4192949.html

edit; There was another Green Chemistry paper, that was currently free to download as well. It is not as feasible, but since it is currently free why not grab it while you can?

Catalytic O-methylation of phenols with dimethyl carbonate to aryl methyl ethers using [BMIm]Cl
Zhen Lu Shen,*a Xuan Zhen Jiang,b Wei Min Mo,a Bao Xiang Hua and Nan Suna
Green. Chem., 2005, 7, 97–99
http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b411201f&JournalCode=GC

The simple answer; impurities!

A major impurity started melting at at about 80*C+ and pulled your amine salt into the molten liquid formed. (There are other factors that will affect melting point, but that is a BIG way off).

It would be a little harder to determine the exact impurities, one would want to look at the reaction that the mixture was born from? You could always just try some of the more popular techniques for purification and you may find something worth while(like below?). If you want we could also try and figure out what it would be, by looking into the precursors and subsequent reaction. But I would imagine there would have been a sufficient work up in the original paper you were working from, or at least a hint as to what it is?

edit; A/B on amines, well the other way around. Take your salt and freebase(is it clear?) wash the freebase and extract with non-polar, wash the nonpolar/freebase thoroughly with water. Then acidify with alot of shaking making sure only to take the aqueous phase, I have found although an old and simple technique it really works wonders pulling especially non-polar compounds out when acidifying as the majority of the non-polars tend to stay in the solvent as the salt preferentially goes into aqueous phase. From there you could reX a couple of times easy enough depending on the compound, that should give you a salt that has a corrected melting point!

Do anyone have a ref for the synthesis of n-acetyl amino acids? I'd imagine it's just reflux with one equivalent of acetic anhydride... Sorry, lazy today

"Anyone knows how to replace Pseudoephedrine OH ring with fluorine? "

Practical and General Method for Direct Synthesis of Alkyl Flouorides from Alchols under Mild Conditions
Babasaheb P. Bandgar1 , Vinod T. Kamble1 and Ankush V. Biradar1
Monatshefte für Chemie / Chemical Monthly

A variety of alcohols were treated with Ph3P and KF in CCl4-DMF at room temperature to afford the corresponding fluorides in very good yields.

http://www.springerlink.com/content/q81173128qx47w77/

"The common method for the transformation of alcohols into alkyl fluorides is substituting the group first with chlorine or bromine and then with fluorine using alkali fluorides. This method is not applicable when the alcohol contains substituents which should not be halogenated for instance double or triple bonds......"

Just another question.....

There is a synth /1/ on Rhodium for P2P from benzyl-magnesium-chloride and acetonitrile. And there is another synth /2/ from the same imine (what is produced from the benzyl-magnesium-chloride and the acetonirile) is to hydrogenated to amph.

The question would be that:
Have anybody tried out the reaction of the grignard reagent and the acetonitrile? On SM /3/ there was someone who tried it out, but he used THF instead on ether and it ruined the whole reaction. He got bad yields with the P2P and there was no other report except what is on Rhodium, so I a bit curious about this part of the synth, but it should work, just a simple grignard reaction with a nitrile. On the other hand, the yields what were reported by Poodle /1/ seems more than good (+75%).

My synth. would go on this way:
React the benzyl-magnesium-halide with the acetonitrile in ether to obtain the imine as it is described in /1/. This product would be filtered out from the reaction mixture. It would be dissolved in MeOH and it would be hydrogenated to amph. with platinum black at atmospheric pressure. The platinum would be filtered off (the magnesium halides also would be filtered out from the reaction mixture) and the freebase or a sulfate salt would be obtained from the MeOH solution.



References
/1/: https://www.erowid.org/archive/rhodium/chemistry/phenylacetone.html#grignard
/2/: https://www.erowid.org/archive/rhodium/chemistry/amphetamine.html
/3/: http://www.sciencemadness.org/talk/viewthread.php?tid=5519#pid64089

The grignard should work.... The hydrogenation should also work... The problem is: this seems too easy.

"Reduction of Aliphatic Nitrites to Amines

Gaudion (Ann,. Chim, Phys., 1912, [viii], 25, 1.25) observed that by passing a mixture of hydrogen and aliphatic nitrites over heated finely-divided nickel or copper, amines are obtained, but he was unable to explain definitely how amines could be produced by the reduction of nitrites. We have also obtained amines by passing a mixture of the nitrites and hydrogen through a heated tube containing reduced nickel, The formation of small quantities of amines by the reduction of aliphatic nitrites can now readily be explained in view of the above experiments. It is the nitro-compounds that are actually formed which undergo reduction to amines, and not the nitrites themselves. Sabatier and Senderens (Compt. rend., 1902, 135, 225) have, as a matter of fact, shown that aliphatic nitro-compounds are thus reduced to amines by hydrogen in presence of heated nickel.

http://www.designer-drug.com/pte/12.162.180.114/dcd/chemistry/nitrite2nitro.html"

As you can see it would be be more advantageous to prepare ethyl nitrite, from the reaction of ethanol with sodium nitrite and sulfuric acid. And produce the hard to come by nitroethane even if it was in low yields, that nitroethane could be further reduced (but why?), it would make more sense reducing nitromethane (with better yields).

@evilblaze;

That seems fine! There was a report by Poodle in one of the links you gave where he returned 75-80% yield.

"The pathway for the conversion of tryptamine to psilocybin and psilocin is still unclear,"

http://www.shroomery.org/6227/The-Metabolic-Pathway-of-Psilocybin-Production

I'm not saying that they don't know, but they might not.