Vibrating_Lights (Hive Addict)
11-12-02 21:44
No 379029
      MDP2P + HEXAMINE  Bookmark   

No matter where swim is he is always thinking chemistry so he had to ask. Could hexamine be used as the amine source in an al/hg. the product could be hydrolozied with HCl after filtering the al sludge giving mda as the product. Well just a thought on the mind
peace
vl-

So much game I could sell a hooker some pussy
Vl_
 
 
 
 
    Rhodium
(Chief Bee)
11-13-02 00:41
No 379072
      Not known in the literature, AFAIK  Bookmark   

It isn't theoretically impossible at least, in light of the recent post on hexamine reduction - Post 378615 (Organikum: "hexamine to methylamine a old new way?", Methods Discourse) - but I doubt that it would be possible to add the hexamine and ketone at the same time to an Al/Hg mixture - but you may be able to do it as a one-pot reaction, as in first adding hexamine and Al/Hg, followed by the ketone and more Al/Hg when the reaction is over.

However, for best yields and purity, first make your methylamine and purify it, then use it for reductive amination.
 
 
 
 
    Moriarty
(Hive Bee)
11-22-02 04:31
No 382080
      Disagreements about acidic amalgamations  Bookmark   

In the past, Someone Who Is Moriarty has had disagreements with other bees about the acidic amalgamation.  Most everyother bee out there says the reaction environment must be basic to work.  I disagree but that's for another time.  Just look up reactionusing the Schiff base and you'll see what I'm babbling about.  Anyway, if the amalgamation must be done under basic conditions then the making methylamine the old way using hexamine/methenamine is just out of the question.  That uses lots of HCl(aq).  TOO ACIDIC!!!  Hydrochloric acid and aluminum?  Hmmm...I believe that would make a sucessful amalgamation impossible.  HCL(aq) + Al is more favorable than the reaction occurring which reduces the ketone.

That means that it would have to be done with hexamine alone but upon looking at the structure of hexamine I believe saturated would be the correct term to use (I might be wrong) but the hexamine wouldn't break down under the conditions of the Al/Hg++ amalgamation.  It won't reduce.   It won't break down under those conditions.  This is just my opinion but everyway I look at it I see failure.  Anybee can correct me if I'm wrong.  I love debate over proposed notions.  It's a good question VL_ but I don't see it. Does someone else have any ideas about it?

P.S. Apologies about responding to a thread that probably belongs in another forum.  It was just too tempting.

Who wants to play cops and dope fiends?
 
 
 
 
    Protium
(Hive Bee)
11-22-02 07:14
No 382157
      Here's one if you got a minute  Bookmark   

I know that you are probably familiar with.....


Dissolve 140g (1 mole) of hexamethylenetetramine (urotropine, hexamine) and 157.5g (1.05 moles) sodium iodide (or 174g (1.05 moles) potassium iodide) in 1000ml of hot 95% ethyl alcohol (190 proof grain alcohol). 243g of bromosafrole (1 mole) is then added and the solution is allowed to stand until no precipitation occurs. A stream of HCl gas is then run into the mixture where the precipitate is hydrolyzed, dissolves and ammonium chloride precipitates. The ammonium chloride is filtered off and the alcohol of the filtrate is removed through distillation under reduced pressure. Purify the crude amine left by releasing the free base with NaOH solution (45g NaOH in 135 ml water). Extract the oil with ether (or toluene, methylene chloride etc.) and reconvert to the HCl salt with a stream of HCl gas. Filter the crystals formed from the ether.

To substitute iodosafrole use 290 grams (1 mole) or chlorosafrole 199g (1 mole). When substituting iodosafrole omit the sodium iodide (or potassium iodide).

../rhodium/chemistry /tcboe/chapter7.html



This is that reaction that you can leave be and go on vacation.

Pr(+)tium
 
 
 
 
    Rhodium
(Chief Bee)
11-22-02 07:27
No 382162
      Br-saf + hexamine = bunk?  Bookmark   

According to ../rhodium/pdf /hexamethylenetetramine.pdf secondary halides are unreactive towards hexamine. I'd really like to hear from a credible source that this reaction actually works...

 
 
 
 
    Protium
(Hive Bee)
11-22-02 12:47
No 382198
      Delpine  Bookmark   

Me too. laugh

Pr(+)tium