Chiral separation of N,N-Dimethyl-1-phenethylamine

[lee]

Can anyone recommend a CSP and mobile phase to achieve an enantiomeric separation of this compound. C6H5CH(CH3)N(CH3)2.
Any suggestions welcome.

[josebenjamin]

Lee,

Compounds of this type are perhaps best separated in two types of CSPs. One is the modified cellulose and amilose columns from Chiral Technologies. Fortunately they have formulated an extensive database where you can see if that compound or similar ones have been resolved that way.

The other possibility I see is to use an enzyme-based column, such as the Ovomucoid (OVM) one. These are perhaps not as rugged as the cellulose ones, but I had good success with similar compounds. The OVM columns used to be available from MacMod Analytical (now part of Agilent I believe).

Good Luck

Josebenjamin

[Cliff Mitchell]

I think for this compound, GC is a good choice. A GC cyclodextrin column would be a good starting place.

If LC is a must, the suggestion of an amylose/cellulose CSP is a good one, the OD or AD seem to be the best starting place.

I would also suggest one of the macrocyclic glycopeptide CSPs from Astec. They are also quite good. I would start with the reverse phase mode, with a mobile phase of 20/80 methanol/TEAA buffer pH 4.1. Or in the polar organic mode with a mobile phase of 100/0.1/0.1 Methanol/acetic acid/tea.

Best of Luck
Cliff

[okara]

Hi,
Try amylose/cellulose base OD, OJ,AS and Ad column with EtOH with 0.1% DEA /Hexane/IPA I hope you will separate the enantiomer if not then try different chiral stationary phase
Thanks

[lee]

All,

Thanks for your advice.

In summary, DAICEL columns i.e AD,OD,AS gave no separation using Hexane and IPA as polar modifier (stopped when IPA reached 2% level).

However, Using cyclodextrin column, from ASTEC, (CYCLOBOND I 2000 SN) mobile phase 15%ACN, 85% Aq. BUFFER (0.1% TEAA) got superb separation. 2.7 mins (R), 4.8 mins (S)

Now a happy camper!!

lee