In this video, we're going to try out a different way of reducing N-Otisim to an amine.

We're basing our procedure on the reference shown, although as you'll see we found that we needed to make some alterations to the workup.

We've been disappointed in the past with some of these reduction references, so let's see how this one goes.

For the reaction we're going to use a 250 mL beaker equipped with a large magnetic stir bar and a thermometer.

Okay, first up is our solvent and one of the reduction reactants.

60 mL of glacial acetic acid.

Let's get this in the beaker.

We've warmed the mixture slightly, and we've got it stirring ready.

Now for our oxim.

This is 12 grams of cyclohexanone oxim.

Check out our previous video for details of how we made this using cyclohexanone and hydroxylamine hydrochloride.

Okay, let's add to the glacial acetic acid and dissolve.

It dissolves pretty quickly.

So we add the rest and get it into solution.

Here we go.

Just for reference, our starting temperature is around 25 degrees C.

Now we've weighed out 21 grams of finely powdered cyclohexanone.

We've added zinc.

We also used a glass bottle and a sheet of paper to make sure that any lumps were broken up well.

Okay, let's start things off and add a little of zinc.

There's no obvious reaction to begin with, so we wait a few minutes and turn up the stirring.

The temperature after a few minutes is 30 degrees C.

Not much at all.

So we decide to add all of the zinc to the reaction mixture.

After a few minutes more with all of the zinc added, there's not much visible change.

But soon we start to see a light ray precipitate and some foam forming.

And the temperature steadily and slowly increases.

Stopping for a second, you can see some white precipitate, the foam on the surface, and some effervescence occurring in the mixture.

Once the temperature reached 80 degrees C, we placed the beaker into a water bath and cooled it back down to around 50.

Once we reached 50 degrees, we took the beaker out of the water bath and then allowed the reaction to continue with stirring for the next two hours.

The temperature rose slightly, and then very slowly cooled.

Instead of filtering the mixture, we decided to steam distill.

So we set out the 500 ml flask with a heating mantle to provide a strong heat source.

And poured in the reaction mixture.

Since any amine will have reacted with the excess acetic acid to form an acetate salt, we need to neutralize the excess acetic acid.

Here we've got 47 grams of sodium hydroxide, which should be enough to neutralize all the acetic acid we started with, plus the total maximum yield of cyclone hexilamine.

Here we've got about 300 ml of oxygen.

Here we've got about 300 ml of ice and water.

We add the sodium hydroxide and the stir to form a solution.

And now we'll add this carefully to the flask containing the reaction mixture.

There's a bit of heat produced, but not excessive.

Here we are with the hydroxide ball added.

Now we set up for steam distillation.

If there's anything amine or ketone like in the mixture, then with a bit of luck it will come over.

Cyclone hexilamine to form an acetate salt with water containing around 80% water and 20% cyclone hexilamine.

Remember that we're boiling a strongly alkaline solution.

So be sure to apply lots of grease to the ground glass joint with the flask.

Because we don't want to risk it.

Well, this definitely looks like an azeotrope of some sort.

And we've got an oily liquid as a separate layer floating on top of the water in the receiving flask.

We left this steam distilled away for about 40 minutes.

After this time the distillate was perfectly clear.

Here's what remained in the boiling flask.

And here's our distillate.

We figured we'd do a solvent extraction on this in order to obtain all the organic components.

So we placed it into a separating funnel.

At this point we could detect an unpleasant amine fishy aroma.

Here's our solvent 15 mls of dichloromethane.

In theory this could react with an amine, but we're hoping that just extracting and

then evaporating it off should be okay.

We've given the mixture a shake and we've got the bottom DCM layer separating.

So we separate this off into a small flask and then we repeat with another 10 mls of

dichloromethane to make sure we've extracted everything.

Here's our organic extract.

We dried this using a little anhydrous magnesium sulfate.

Then we decanted this into a pre-weighed dry flask.

And then evaporated off the DCM solvent using a warm water bath and a vacuum.

Okay here's what we ended up with.

Just slightly over 11 grams of a clear color close slightly oily liquid with a volume of

about 11 mls.

It's got a really unpleasant fishy aroma.

But also with the spicy characteristic aroma of cyclone hexanone in there as well.

So it's not completely pure.

Let's do a quick rough test to see if we can see how much ketone there is.

Here's some 10% dilute sulfuric acid.

Let's add a small amount of the product and see if it reacts and dissolves.

Well there's definitely a reaction.

And with swirling it looks as though most of it dissolves.

So it's going to need some further purification.

But it looks as though this method dish work has a way to reduce auxams to amines.

We've got no plans for our cyclone hexalamine but we'll have to think of one for a future

video.

Thanks for watching.

And stay tuned.

I'll see you next time.

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