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Topic: Can I hydrogenate C/N bond like this...?  (Read 1537 times)

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Offline Altered State

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Can I hydrogenate C/N bond like this...?
« on: March 23, 2013, 04:11:01 PM »
I need to get aminomethylciclohexane from butadiene and arylonitrile.

I proposed Diels-Alder reaction between them, and then, total hydrogenation using H2 and Pt catalyst.
Is that allright? Can I hydrogen triple CN bond like that?

Offline Dan

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Re: Can I hydrogenate C/N bond like this...?
« Reply #1 on: March 23, 2013, 06:51:18 PM »
I believe so, yes. The conditions may need to be fairly forcing though (heat and pressure), but I don't know a great deal about catalytic hydrogenation of nitriles. I think Raney Ni might be a more common choice of catalyst for this, but I'm pretty sure you can use Pt and Pd as well.
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Offline discodermolide

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Re: Can I hydrogenate C/N bond like this...?
« Reply #2 on: March 23, 2013, 10:05:06 PM »
If I make chip in.
Raney nickel is the catalyst of choice here. You use 10%NH3 in ethanol as a solvent at normal pressure, heat if you must but that is usually not required. The ammonia prevents the formation of secondary and higher amines. After work up you can isolate the new amine by making the HCl salt.

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