Sorry the 4-piperidinone previously discussed (N-Phenethyl-4-piperidinone) is condensed with o-flouroaniline.

Its pretty straight forward! You can use a magnetic stirrer for up to 1 liter easily if you have a good stirbar and stirrer. But I know of people that have stirred then left overnight without further stirring and everything turned out fine. I would focus on the subsequent reduction as thats harder than oximation.

Cough..Cough..Zinc dust (2.6 eq.) and copper sulfate (1.4 eq.) were suspended in 65% aqueous ethanol and sonicated (Bransonic 1200) for eight minutes at 60°C, then a solution of oxime was added, and the reaction continued for approximately three hours. Cough. Cough...Cough....

Wow thats a bad cough, lucky no one saw as it would have appeared I was spoonfeeding you

That's right

If an Ether Solution of Ammonia is added to an amine salt this should covert the Salt into freebase + Ammonia chloride correct? Just like basifiy but no water present but im assuming the mechanics should stay the same I just want to be sure.

Not short, but question....

So:
The main idea would be to make 3,5 dimethoxy 4 ethoxy benzaldehyde from vanillin. The reaction would go in 3 steps:


In the first step the vanillin would be reacted with bromine to form 5 bromo vanillin. This is a simple halogenization in GAA, according to /1/

The second step would be reacting the 5 bromo vanillin with sodium methoxide. The idea is to make a NaOMe solution from sodium and methanol and add this solution to another solution what is 5 bromo vanillin dissolved in MeOH. NaBr crystals should be filtered and the solution should be diluted with water, the 5 methoxy vanillin should be extracted with ether. Actually no reference, but this is not a hard reaction....

Now let's see the problematic part... The alkylation with diethyl malonate [This should probably be oxalate - Enkidu]. This reaction works with most phenols, according to ref /2/. The question part is, that how to separate the different compounds.... Maybe a column chromatography would be a good idea... Or react the remaining phenol with something.... FeCl3 or just make a sodium salt with NaOH what is less/or not soluble in ether. Any ideas?

Or start the reaction with the alkyltion of the vanillin with diethyl malonate... But the problem is still there...  4 ethoxy vanillin is not easily separated from the vanillin.

And I want to use "OTC" ethylting agent and not diethyl sulfate or something like that...

Any ideas?

/1/: http://www.erowid.org/archive/rhodium/chemistry/mmda.mescaline.html
/2/: Read the pdf what is posted....

I am wondering about chlorinating amino acids. Can it be reasonably done? Would a strong chlorinating agent like phosphorus pentachloride be able to do the trick? I just had a window about it open but I won't be back until tomorrow so I thought I might as well throw it out there first.

You must have seen the post I made yesterday!

PROCESS FOR THE PREPARATION OF 2,4,5-TRIMETHOXYBENZALDEHYDE
The title has a typo, it is really 3,4,5-trisubstututed
http://www.freepatentsonline.com/3855306.html

Novel highly selective catalytic oxychlorination of phenols
Luciano Menini and Elena V. Gusevskaya
DOI: 10.1039/b513329g

I didn't saw your post, the idea was based on, that I got some pure vanillin recently and what can be this thing used for?

The original synth is doesn't looks too good for me, everywhere they use dimethyl sulphate, dimethyl carbonate, trimethyl phosphate and so on... These are not so friendly chemicals and they are not easily obtained. This why I want to go on an easier way.

My last post was wroted at 2 a.m. and the malonates in the text are oxalates.... I was really tired... Sorry.

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....

Suppose you have a mixture of a the following because I think something would be strange if this was the case,,,,

You have,
    A heavy amine with a high BP and
    Ammonia gas dissolved in the following mixtue of solvent.
    The solvent system consist of (highest to lowest)Heptane and Diethylether.
    The entire system would be anhydrous
   
All Non solubles could have been filtered completely to leave a light yellow Solvent solution.
This solutions volume could have been completely reduced until no more Ether is smelled leaving a small amount of semi thick golden oil smelling of amine
This is done to remove the solvent that contains the Ammonia.
There is only a trace of oil left over prehaps some Heptane due to its closeness to the BP of water which it was evaporated on.(a low temperature water bath) but it mostly smells of amine.


Now if this was the case and someone did all of these perimeters and attempted to add Muratic acid to the oil in an attempt to turn the amine to its HCl salt and had the following unusuall thing happen what would be your explination?

When the fumes of HCl (and when slowly dripping in) the HCl forms wisp of smoke simular to ammonia chloride vapors. This person thought ok maybe in an unlikely event its ammonia still present so they made damn sure to reduce the volume as much as can be and added IpOH and evaporated again to try to entrain any NH3 that might bet here to leave. This still Occured no matter what was done.

To make matters worse there is oil present that no matter how low this person makes the PH it still is present and worst of all still smells of amine even though evaporation yeilds amine hcl crystals with contamination....

Has anyon ever added 34% HCl slition directly t warm Freebase amine and seen wispy smoke?


Side question..... Whats does Heptane smell like. Is there any way it could be confused with amine smell?

How do you know that you only have the amine (besides solvent and ammonia) in there? maybe the oil is a side product or an unreacted precursor to your amine...