Re: ORGLIST:procedure for the reduction of a aliphatic secondary amide

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From: Manuel Toennis (mt$##$org.chemie.tu-muenchen.de)
Date: Mon Feb 03 2003 - 08:04:49 EST

Try fresh(!) LAH, at least 100% excess (not all 4 H's have the same reactivity,
usually only 2 really react), in dry(!) ether, reflux overnight, then reaction
control (NMR), continue reflux if necessary. (you most probably cannot separate
product and educt, so you better have 100 % conversion ;-). Workup: add with
good cooling dropwise concentrated aquous ammonia-solution through the refulx-
condenser, if the gas/heat-development is over then continue adding until
the 'aquous' phase gets slimy-liquid. pour off the organic phase, wash the
residue by stirring with more ether, dry, evaporate. usually 97%+ yield.

Hope that helps,
MT

Zitiere "Research Scholars,tpr" <tprscrs$##$uohyd.ernet.in>:

> Dear all
> I have prepared a long chain secondary
> amide(N-ethyl-octadecylamide).
> I want to reduce this to the corresponding sec. amine. LAH and
> DMSO+Methane sulphonic acid are not reducing this amide. if you can
> suggest any other procedure to reduce this Sec. aliphatic amide it will
> be
> very useful for me.
> thank you.
>
> with regards
> MSC.
>
>
*******************************************************************************
> Research Scholar Email:tprscrs@
> Dr. T.P.Radhakrishnan's Group uohyd.ernet.in
> Theoretical & Material's Chemistry Group
> Tel:(040)-3010500
> School of Chemistry x-4827, 4750
> University of Hyderabad
> Hyderabad-500 046
> India
>
*******************************************************************************
>
>
>
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