Sciencemadness Discussion Board

N,N-diethylamino-ethyl chloride synthesis

liftedresearch - 17-1-2016 at 17:34

Hello all,

I am interested in synthesizing N,N-diethylamino-ethyl chloride, to me, it seems to me to be a chlorinated triethylamine. If this is so, how would i go about chlorinating the triethylamine? I am asking not for a in depth explanation, but rather a reference or a general idea of how it would be done. Thank you in advance


Crowfjord - 17-1-2016 at 17:44

The two are structurally related. It is the chlorinated analog of triethylamine. However, just because two molecules are structurally related, it doesn't always mean one may be converted to the other. The diethylaminoethyl chloride could, in theory, be made from triethylamine, but in practice a lot of other crap would probably be formed in the process.

I think that N,N-diethyl-ethanolamine would make a better starting compound. Chlorinate the alcohol with any of a number of reagents.

[Edited on 18-1-2016 by Crowfjord]

Chlorinating agent

liftedresearch - 17-1-2016 at 18:28

Thank you for your quick and helpful response. What would you consider the best chlorinating agent, i am not too familiar with chlorination reactions som please have some patience. Would sulfuryl chloride or thionyl chloride be effective; or would some other chlorinating agent be necessary? A reference would be helpful, and quite frankly a decent amount of entertainment. once again thank you for the quick reply and help.

Crowfjord - 18-1-2016 at 15:23

Here's one that uses thionyl chloride, from JACS Vol 66 pp 1921-1924 (1944):
Quote:

Preparation of @-Diethylaminoethyl Chloride.--In a two-liter three-necked flask equipped with a mercury- sealed stirrer, dropping funnel and reflux condenser (with a drying tube) was placed 205 g. (1.75 moles) of &diethyl- aminoethyl alcohol (Eastman Kodak Co.) dissolved in 500 ml. of dry thiophene-free benzene. The flask was chilled in an ice-salt-bath and 230 g. (1.93 moles) of thionyl chloride was added slowly with stirring. The reaction mixture was then allowed to warm up to room temperature and refluxed six hours on a steam-bath. The mixture was cooled, the dark precipitate filtered off and washed with dry benzene, the &diethylaminoethyl chloride hydrochloride being ob- tained as a brown solid; yield, 286 g. (95%).



Some others use sulfonic acid chlorides like p-toluenesulfonyl chloride or methyl sulfonyl chloride. I bet concentrated HCl and zinc chloride (Lucas' Reagent) would work, too. That would probably be a bit more amateur-friendly.