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Topic: reduction of oxime H-donor process  (Read 4953 times)

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Offline bmorvan

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reduction of oxime H-donor process
« on: March 11, 2011, 09:27:28 AM »
There are many interesting processes for reduction of oxime to amine. Perovskites with iPrOH, Zn with ammonium formate.. But all the molecules are non soluble in water.    How to isolate the final amine when it is soluble in water?
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Offline enahs

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Re: reduction of oxime H-donor process
« Reply #1 on: March 11, 2011, 01:23:25 PM »
First you said non soluble in water then soluble...which is it?

And just because it is soluble in water does not exclude it from being soluble in organic as well, in which you can extract. And you can often help drive it out of the water into the organic by increasing the ionic strength of the water like crazy.

Offline Dan

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Re: reduction of oxime H-donor process
« Reply #2 on: March 11, 2011, 03:08:49 PM »
Very polar amines can also be purified by ion exchange chromatography.

If the reaction is clean/does not contain other amines as impurities, you can simply load the reaction mixture onto a short column of a strongly acidic resin (I used to use Dowex 50W X8 for this regularly). The amine is protonated and immobilised on the resin, you can then wash off salts etc with water, and finally liberate the amine by flushing with dilute aqueous ammonia. If you have a mixture of amines you can use various resins to separate amines in a more rigorous chromatographic purification (e.g. Amberlite, phosphonics cartridges etc.). There is also reversed phase chromatography as well.
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Offline bmorvan

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Re: reduction of oxime H-donor process
« Reply #3 on: March 12, 2011, 04:08:05 AM »
All amines proposed are aromatic, it means non soluble in water Mine is soluble in water and non soluble in organic solvent.

About chromatography I have to produce 1 kilo.
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Offline Dan

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Re: reduction of oxime H-donor process
« Reply #4 on: March 12, 2011, 05:52:01 AM »
Recrystallisation? Distillation?
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