Amines can be synthesized through multiple methods including reductive amination (from aldehydes/ketones with ammonia, building from primary to secondary to tertiary amines), nitrobenzene reduction (using iron and acid to reduce nitro group to amine), azide synthesis (from alkyl halides via alkyl azide reduction), carboxylic acid conversion (via acid chloride to amide then reduction), Gabriel synthesis (using phthalimide, potassium phthalimide, R-group addition, and hydrazine), and nitrile reduction (from alkyl halides via nitrile formation then reduction).
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Amine SynthesisAdded:
And specifically what we just covered was different ways to form an amine.
Mhm. So we saw that here with reductive amination where yes, we could either go from an aldehyde or ketone, use ammonia, and then notice we're just going to form a primary amine. Yeah. Versus when we have a primary amine, we now are going to form a secondary amine. Mhm. So it kind of like builds from there, right?
>> Right, so yeah. Now a secondary amine is going to give us a tertiary amine. And we keep going from there. It looks a bit different from what we just saw with the aldehyde.
>> Mhm. Like the positioning of the amine, right? Where instead when we had an aldehyde here, the NH2 was on this side, right? On that end. So understanding that yes, it does kind of switch a bit, but it still would have been a primary amine.
>> That makes sense, okay. Next, another way. Does this look familiar? Mhm. Going back to reactions of aromatic compounds.
>> Yes. Right, we have a nitro benzene and it doesn't matter which one we decide to use. There is a bunch of these that we can choose from. I'd say the majority of the time you're going to see iron and then acid be used and then the second step. Oh, okay. That's good to know.
And then of course this reduces that nitro group to amine. Mhm. Definitely know this one, hint hint.
>> That's good to know. Then we just covered the azide synthesis where we went from an alkyl halide, then we went to our alkyl azide, then whichever reduction you decide to choose, that will give us a primary amine.
>> Okay. We also looked at this before with our carboxylic acids where we saw, okay, I have a carboxylic acid, I'm now going to change this to my amide using these two steps.
>> Mhm. And I know that first step would have converted it to an acid chloride.
Mhm. Then with the second step I get an amide. Then finally reduction gives me an amine.
>> Okay. Gabriel synthesis, we also looked at that, right? We have phalamide, which is what this is called. Then we have this entire portion of it where there's three different steps where we're going to make this into potassium phalamide.
Then from there we add an R group, then from there using hydrazine, we then form our primary amine. Okay. And the last thing here was another type. This goes back to SN2 reactions and reduction of nitriles. Mhm. Where I start off with an alkyl halide using either one of these, I then form that nitrile. Then I reduce the nitrile using any one of these combinations for reduction and then I form my primary amine.
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