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Reducing amides to amines

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I've been interested in psychoactive substances for some years but never been able to solve this task.
Cheap converting amides(-CO-NH-) to amines (-CH2-NH-). I've tried LiAlH4 in ether or hydrocarbon medium but it seems to be very expensive.
Do someone know how to do this cheap?
And another one, the 3D formulas where the N in sp2 is connected to sp2 carbon in TIKHAL are not exact.
The sp2 Nitrogen forms 3 valen bonds with the sp2 electrons and with the 2p z. where the electron couple is situated makes p-pi interaction with the pi bond of the sp2 carbon, so the structure is planar (like NH2-NO2) and not triangle piramid. Anyway, it can turn to triangle pyramid if you heat the compound.
For more info on the subject see urea quantum structure.

The usual method besides using LAH in ether is catlytic hydrogenation using copper chromite catalysts, at 200 to 300 atmospheres and 250 to 265 °C, yields are often low due to side reactions, cleavage et cetera  ::)  Alternatively, the same reduction has been done electrolytically, see Bull Chim Soc Fran 12 773 (1945) for more details  :)

A must have article for electrolytic reduction:
'Electrolytic Reduction of Organic Compounds' Chemical Reviews vol 62 pages 19-40 (1962)

Electrolytic reduction of amides to amines:
Zhurnal obshchii khimii (J. Gen. Chem. USSR) 17, 1651 (1947)
Zhurnal obshchii khimii (J. Gen. Chem. USSR) 11, 51 (1941)
Bull. Chem. Soc. Japan 11, 41 (1936)
Trans. Electrochem. Soc. 84, 165 (1943)

Catalytic hydrogenation of amides to amines:
JACS 56, 247 (1934)
JACS 61, 3449-3502 (1939)
Patent US2187745

Many amides can be reduced to amines by triacetoxyborohydride formed in situ from sodium borohydride and glacial acetic acid.

This method is sufficient for many amides:

To a suspension of the amide, toluene and sodium borohydride is added GAA dropwise without cooling. When the acid has been added the mixture is allowed to stir for one hour with or without heating. The reaction progress is checked with TLC. Destruction of excess hydride and standard A/B workup gives amines in the range of 40-80% of the theoretical yield. In many cases trifluoroacetic acid gives better yields than acetic acid.

All amides are not alike.  Some are harder to reduce than others.  Some are very resistant to reduction.  N,N-dialkylamides are easier to reduce electrolytically than N-alkylamides and N-alkylamides are easier to reduce than non substituted amides.  Get that Chem. Rev. article and read it.


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