Waffles SS
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N-(1-Naphthyl)ethylenediamine
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This compound can be prepared by the reaction of 1-naphthylamine with 2-chloroethanamine
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I dont think this is possible to make N-(1-Naphthyl)ethylenediamine from 1-naphthylamine with 2-chloroethanamine.I think self condensation of
2-chloroethanamine free base will happen.
Someone has better idea or method for making it?
[Edited on 23-12-2013 by Waffles SS]
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Dr.Bob
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The simplest way to make that would be a Buchwald RXN on 1-naphthylbromide with either 1,2-diaminoethane, or better, the mono-protected version.
BocEDA is ideal for that. That would be ideal.
Alternatively, if you have the amine already, I would do a reductive amination with Boc-Gly-aldehyde, that works well.
The 2-ClEtNH2 might polymererize, plus it will react with the product to form oligomers. That is why most people use mono-protected amines for these
reactions or maybe Boc or Cbz-amino-ethylchloride instead, that might be stable to the conditions you suggested.
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Waffles SS
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Thanks Dr.Bob ,
Do you have detail for that reaction(Buchwald RXN on 1-naphthylbromide with ethylenediamine)?
What about 2-Nitroethylamine?
Reaction of 2-Nitroethylamine with 1-naphthylchloride and then reduce NO2 to NH2 by Fe/HCl?
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DJF90
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How about conjugate addition of the 1-naphthylamine to 1-nitroethylene, followed by reduction of the nitro group?
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Waffles SS
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@DJF90 that is interesting.
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Nicodem
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Thread Moved
23-12-2013 at 09:57 |
DJF90
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The requisite nitroethylene can be made by dehydration of 2-nitroethanol with phhalic anhydride. OrgSyn mentions this in the discussion section of
2-nitroethanol, which is formed from formaldehyde and nitromethane by Henry reaction. If I'm not mistaken, a procedure for 2-nitropropylene is also
given in OrgSyn, and the dehydration step in particular is explicitly described. It ought to be applicable to the nitroethylene prep too.
Regarding storage of the nitroethylene: I recall something saying a 10%w/w solution in benzene keeps well at 10*C. I'm sure you can find the
appropriate paper for the finer details.
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Waffles SS
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Thanks DJF90,
What about imidazolidinone?
As @PHILOU Zrealone mentioned this is possible to selective alkylation of Ethylenediamine by Imidazolidinone
http://www.sciencemadness.org/talk/viewthread.php?tid=25527#...
In this case we just need to attach one Naphthalene to one of the Nitrogen on Ethylenediamine(reaction of Naphthyl Chloride or Bromide with
Ethylenediamine) and i dont know this is possible or not.
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UnintentionalChaos
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There's also this: http://www.orgsyn.org/Content/pdfs/procedures/cv9p0636.pdf
Nitroacetaldehyde diethyl acetal which would probably readily condense with 1-naphthalamine to N-(1-naphthyl)-2-nitroethanimine. A serious dose of
reducing agents would bring about the desired product (perhaps in two steps, something mild to reduce the imine followed by something stronger to
reduce the aliphatic nitro group.)
[Edited on 12-24-13 by UnintentionalChaos]
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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Waffles SS
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thanks @UnintentionalChaos ,
one of my friend suggest below method :
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Starting from 1-aminonaphthalene and glycolaldehyde, you make 2-(Naphthalene-1-ylamino)-ethanol via reductive alkylation with STAB (sodium
triacetoxyborohydride).
Second step, chlorination with thionyl chloride, gives you (2-Chloro-ethyl)-naphthalene-1-yl-amine hydrochloride. Use low temperatures (not higher
than room temperature) here to avoid self-condensation and an excess of thionyl chloride.
Third step, reaction of the hydrochloride with a hefty excess of conc. ammonia solution (approx. 500-1000 fold molar excess, but ammonia is dirt
cheap; use a 1:1 mixture of alcohol and strong ammonia) yields your desired N-(1-Naphthyl)ethylenediamine. Instead of the fast method with ammonia,
you could also use the Delepine or the Gabriel reaction, but I leave this choice up to you
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DJF90
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Seems reasonable.
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Waffles SS
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What about reaction of Ethanolamine-O-sulfate(2-Aminoethyl hydrogen sulfate) with excess 1-Naphthyl amine?
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2-Aminoethyl hydrogen sulfate prepare by Esterification of Ethanolamine (H2N-CH2-CH2-OH)with sulfuric acid.
PREPARATION OF 2-AMINOETHYLSULFONIC ACID
Galuh Widiyarti*), Muhammad Hanafi, Siti Isnijah, L. Broto Sugeng Kardono, Ermawan,Ngadiman, and Andini Sundowo
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[Edited on 25-12-2013 by Waffles SS]
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