coniine from hemlock

Recently I discovered a huge hemlock field near my house. I thought it might be interesting to try extracting coniine from the hemlock.
After a bit of research I formulated a procedure and carried it out:

To a 1000ml round-bottom flask I added 42g of hemlock cuttings and 24g of sodium bicarbonate dissolved in 300ml of water. I set up for simple distillation and distilled the mixture. I collected 290ml of liquid. Unfortunately the liquid in the distilling flask foamed considerably and a lot of the foam passed through the condenser and into the receiving flask . My distillate was green. I decided this wasn't a huge problem and continued on. I added dilute sulfuric acid to my distillate until it became acidic. I then boiled my acidic mixture down until 90ml of liquid remained.

Since the coniine had been converted to a salt by the H2SO4 I expected it would not boil off. Anyway the 90ml of liquid was chilled down then adjusted to pH 12 with 4M NaOH solution. There were a few solids in my mixture so I filtered them off. It was at this point that I noticed the smell of the mix became very stinky, because the coniine had just been free-based maybe? Anyway, I added and mixed 100ml of dichloromethane into the mixture to extract the coniine. Once the dichloromethane phase had completely separated out, I drained it into a distilling flask and using a water bath I collected the dichloromethane that boiled at 40-45 C. I thought I would be left with my coniine which boils at 166 C, but after the dichloromethane distilled over, nothing was left.

could someone please help me come up with a fool-proof way to extract the coniine? were did i go wrong?

thanks in advance

@JJay so the freebase coniine is soluble in benzene but the hydrochloride salt isn't, so gassing the benzene extract with hydrogen chloride precipitates coniine hydrochloride.
Is that right?

I'm planning on making some benzene soon so I guess I can try this out. Thanks for the idea.

I don't mind having a bit of conhydrine, methylconiine etc in my product. If I ever get a chromotography column, I might try purifying the coniine

@j_sum1 I understand coniine is a very potent toxin. I used gloves, a respirator, and an apron during my attempted extraction. The work was performed outside. Thank you for the warning . Coniine must absolutely be treated with the respect it deserves.

It does unnerve me a bit that I don't know where the coniine ended up...

@Draconic acid, I didn't really plan to use the coniine for anything (just keep it as a sample). However, coniine transition metal complexes sound interesting. I wonder if copper forms a complex with coniine.

Thanks for the feedback everyone!


[Edited on 22-4-2016 by gluon47]

[Edited on 22-4-2016 by gluon47]

Quote: Originally posted by gluon47

@JJay so the freebase coniine is soluble in benzene but the hydrochloride salt isn't, so gassing the benzene extract with hydrogen chloride precipitates coniine hydrochloride. Is that right?

Quote: Originally posted by gluon47

@Draconic acid, I didn't really plan to use the coniine for anything (just keep it as a sample). However, coniine transition metal complexes sound interesting. I wonder if copper forms a complex with coniine.

Quote: Originally posted by JJay

Oh and you could get away with using toluene instead of benzene.