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Re: ORGLIST: amine extraction

From: Ken Knott <kknott>
Subject: Re: ORGLIST: amine extraction
Date: Sun, 27 May 2012 09:51:37 -0400
Did you ever try washing the organic layer with a saturated solution of LiCl or LiBr?  In my experience with will routinely remove the DMF.

On Sun, May 27, 2012 at 7:53 AM, vinutha hanumaiah <> wrote:
Hi nema., 
I tried making t salt but DMF stays in t acidic layer and removing DMF from t acidic layer is again a tedious as it is not able remove dmf completely. Am planning to remove the DMF under high vaccum pressure from t acidic layer or vil hav to try 10% LiCl soln wash n check.. If DMF can b removed completely or not. 
Any comments welcomed. 



On Sunday, May 27, 2012, nima ghonouei wrote:
if the problem is DMF not the pyridine, u may crystallize pyridine and your amine in a form of a hydrochloric salt.

On Sat, May 26, 2012 at 5:03 PM, vinutha hanumaiah <> wrote:
Hi Andrew,
I have tried azeotroping, since the compound is highly polar and low boiling point finding difficult to extract the pure copmound.

On Sat, May 26, 2012 at 8:15 AM, Andrew Molder <andrew.molder> wrote:

Have you tried azeotroping your purified compond a couple times on the rotovap?

On May 25, 2012 10:21 AM, "vinutha hanumaiah" <> wrote:
Many Thanks Peter,

On Fri, May 25, 2012 at 8:27 PM, Petr Melsa <melsap> wrote:
Try to dissolve you compound in diethyl ether of ethyl acetate and wash with 5% aq. lithium chloride a couple of times.

Good luck,


On Fri, May 25, 2012 at 3:38 PM, Ilya Avrutov <IAvrutov> wrote:
W=Hi Thanu,

What else your compound soluble in? If it soluble in some
water-immiscible solvents, you could try to saturate aqueous solution
with NaOH and extract the produt in another solvent. I think DMF will
remain in aqueous layer mostly.


-----Original Message-----
From: orglist-everybody
[mailto:orglist-everybody] On Behalf Of thanu
Sent: Friday, May 25, 2012 8:44 AM
To: OrgList
Subject: ORGLIST: amine extraction

Hi all,

I have prepared a moity which has pyridine and a secondary amine in it
by substitution reaction. The reaction was done using DMF, the issue is
I tried workup using acid-base method but was not able to remove DMF
fully. Also i cant use high vaccum coz the compound has a low boiling
point. Can anyone suggest a method to remove DMF at low temperatures? My
compound is soluble in cold water too and the reaction was done in THF
which didnot work. Hiope for better solutions from any of u.

Thanks n regards,


"It is difficult to find a black cat in a dark room, especially if there is no cat."

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