Sciencemadness Discussion Board - Morpholine derivate from secondary amine/alcohol


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Sciencemadness Discussion Board » Fundamentals » Organic Chemistry » Morpholine derivate from secondary amine/alcohol

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Sauron

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posted on 13-1-2009 at 09:51

Be extremely careful that you do not have any intermediate or product with a halogen beta to either the N or the O, because if you do you will have either a nitrogen mustard or an oxygen analog of same. You do not want to be around either.

What's this about not knowing where to get ethylene glycol?

Antifreeze. Some are EG, others are propylene glycol, some mixtures. Go to an auto store or hardware store and read labels.

Hydrobromic acid? Make your own or use conc H2SO4 + NaBr.

But heed my warning. -N-CH2-CH2-Br is a bad idea.

(BrCH2CH2)2N- is a worse idea.

Sic gorgeamus a los subjectatus nunc.

smuv

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posted on 13-1-2009 at 20:46

Quote:

Originally posted by jon
right, that's what he's driving at, 2-iodoethanol, k2co3, ephedrine, and methanol reflux it.
but why bother? that's a shit compound you want phenmetrazine the routes are cloroacetylchloride to phenylpropanolamine, followed by cyclization with koh and reduction with LAH.
or oxalyl choride and ppa and lah reduction.
or you could get *creative* and react iodo ethanol with ppa in dmf with CsOH to suppress dialkylation distill the hydroxyethylamine and cyclizize with conc. h2so4 via the concerted reaction they talk about.

I don't really think the methods you proposed are any easier.

Tertiary amines do not form as readily as in other alkylation reactions because the product is a weaker nucleophile than phenylpropanolamine. This is simular to the synthesis of glycine from B-chloroacetic acid, where the electron withdrawing character of the carboxylic acid makes glycine a weaker nucleophile than ammonia, therefore mono alkylated products predominate.

Also, sterics plays a factor in this case...

[Edited on 1-14-2009 by smuv]

"Titanium tetrachloride…You sly temptress." --Walter Bishop