liftedresearch
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4-(2-Chloropropyl)morpholine synthesis
Hello all,
I'm looking to synthesize 4-(2-Chloropropyl)morpholine but am at a standstill. I'm not looking for any handouts, just someone to point me in the right
direction.
Thank you
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CuReUS
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You could just react morpholine with propylene oxide and then convert the OH to Cl or react morpholine with allyl chloride or allyl alcohol and then
add HCl
[Edited on 2-4-2017 by CuReUS]
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liftedresearch
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Thank you, so for the allyl alcohol route, what are the reaction conditions? Or a ref?
Thanks again
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CuReUS
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apparently,allyl alcohol cannot be used directly to alkylate morpholine easily.You need to first convert it to its acetate or benzoate ester and then
react it with morpholine in the presence of a Pd catalyst to achieve alkylation.There is a way to react allyl alcohol directly but you will need a
Ni(cod)2/PPh3 catalyst.I could give you the refs if you want,but they aren't easy.
a more OTC and amateur friendly method would be to convert the allyl alcohol to the halide and then react that with morpholine
alkylation using allyl chloride - http://www.sciencedirect.com/science/article/pii/S0959943605...
alkylation using ally bromide - http://www.tandfonline.com/doi/full/10.1081/SCC-120021838
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Nicodem
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Thread Moved
2-4-2017 at 03:39 |
liftedresearch
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So I suppose it would be far easier just to use allyl chloride. Taking that route, would I just mix equimolar amounts? Should there be an excess of
one reagent? The reason. I ask is because I dont have access to the ref you gave me.
Thanks once again
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liftedresearch
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I apologize for the lagged response time, how would the propylene oxide alkylate the amine? And where would the hydroxyl group end up? I also thought
of chlorinating 2 methyl 1,3 propane diol and then using that to alkylate the morpholine, this way I alkylate and keep a chlorine atom on the terminal
carbon. Tell me what you think it is greatly appreciated.
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CuReUS
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Quote: Originally posted by liftedresearch  | | I apologize for the lagged response time, how would the propylene oxide alkylate the amine? And where would the hydroxyl group end up?
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https://goo.gl/images/TjVSJu
| Quote: | | I also thought of chlorinating 2 methyl 1,3 propane diol and then using that to alkylate the morpholine, this way I alkylate and keep a chlorine atom
on the terminal carbon. |
the Cl in your target compound is not on the term carbon, its on the secondary C
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