Sciencemadness Discussion Board

selective extraction of DL-methylbenzylamine instead of fractional crystallisation

karlos³ - 28-9-2019 at 14:00

I've already asked this in the short question thread but according to my experience fewer will see it there.
The question is, if I can apply the following procedure(to be found under selective extraction): https://erowid.org/archive/rhodium/chemistry/amphetamine.res...
On the racemic 1-PEA amine.
I used the procedure above(and a few others did too) successfully on the "phenylisopropylamine", only using toluene instead of benzene.
It is a well working and way more easier procedure that waiting for one enantiomer to crystallise out fractionally.
Now that I have made plenty of 1-PEA via different routes actually(acetophenone amination with Ni/Zn, oxime reduction with ammoniacal Al/Hg etc), I want to chirally resolve it too just for the sake of it.
Please help! Any objections why it should not work with a two phase system of toluene and water with monosodium tartrate?

[Edited on 28-9-2019 by karlos³]

UC235 - 28-9-2019 at 14:33

I did 1-PEA resolution with tartaric acid as an undergraduate experiment. There's probably a j chem ed paper describing it in that case. The diasteromeric pair crystallizes out and we measured optical rotation of the solid and supernatant.

Yes: http://sci-hub.tw/10.1021/ed042p269

[Edited on 28-9-2019 by UC235]

karlos³ - 28-9-2019 at 14:51

Yeah I know that but thank you for that.
However, I want to proceed differently and want to resolve their enantiomers via selective extraction using the monosodium tartrate salt instead.

[Edited on 28-9-2019 by karlos³]

UC235 - 28-9-2019 at 19:42

If it works on amphetamine, it should work fine on 1-PEA. might have to adjust concentrations but shouldn't be far off.

karlos³ - 29-9-2019 at 04:05

Ok thanks, that is what I wanted to hear :)