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Imines to amines with Zn/5% aq NaOH

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GC_MS:
Gives me an error msg when i want to read the first page, chemistris
WOMAN.ZIP: Great Shareware, but be careful of viruses...

Cyrax:
There was no error when I viewed it, GC_MS (with acrobat reader V5.0).

In example 1h, they condense benzaldehyde with methylamine, the yield is only 53 %  :( .

I hope an optimized procedure can be found for P2P ...

GC_MS:
SWiM dls with opera and the pdf is fux0red; he dls with IE and it is fine. wtf?
Cyrax: yields look low indeed  :( ... Deriving from 1a-1c, single substituents don't seem to have that much of an effect.
WOMAN.ZIP: Great Shareware, but be careful of viruses...

thewire:
Hydrogenation Reactions of ketimines and aldimines

2. Reduction using metals
4. Sodium borohydride
Harada, K.; Patai, S. The Chemistry of the Carbon Nitrogen Double Bond; John Wiley and Sons,
Inc.: New York, 1970;pp. 276-298

A mixture of methylamine and m-methoxybenzylmethyl ketone yields the corresponding N-methylamine by reduction with aluminium and water (equation 110) ref. 118

118. G. Hildebrandt, U.S.Pat. 2,344,356 (1944);Chem. Altstr., 38, 3421 (1944).
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Organic Reaction in Water. Part 1. A Convenient Method for Reduction of
lmines Using Zinc Powder

Tetrahedron Letters 39 (1998) 8873-8876
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A simple and efficient method for the preparation of secondary N-alkylarylamines via reductive amination of ketones with primary aromatic amines using activated zinc/acetic acid is described. It requires only equimolar amounts of the starting compounds and affords good yields of the corresponding amines (50-90%). It is not applicable to aldehydes nor aliphatic amines

Synthesis, 1991, 11, pp. 1043-1045
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Reductive Amination with Metallic Magnesium
J. Chem. Soc. Perkin Trans. 1, 265-269 (1995)

https://www.erowid.org/archive/rhodium/chemistry/redamin.magnesium.html
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thewire:
121. H. Schonenberger, H. Thies and A. Rapp, Arch. Pharm., 298, 635 (1965)
Der Einfluß von Lösungsmitteln auf den Verlauf der Reduktion Schiffscher Basen mit aktiviertem Aluminium (pages 635–638)

When benzylidenealkylamines (41) and ethanol are treated with activated aluminium, a
mixture of benzylalkylamines (42) and NN'-dialkyl-a-a'-diphenylethylenediamines (43) is obtained (equation 112) ref 121.

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Cp2TiCl2 catalyzed reduction of imines by isopropyl magnesium bromide

Abstract  Refluxing RCH:NR1 (R = Ph, 4-ClC6H4, 4-MeOC6H4, 4-Me2NC6H4; R1 = Ph, 4-ClC6H4, 4-BrC6H4, Bu, cyclohexyl) with Me2CHMgBr in the presence of dicyclopentadienyltitanium dichloride in Et2O gave 66-93% RCH2NHR1.

http://sioc-journal.cn/Jwk_hxxb/EN/abstract/abstract335004.shtml#
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A new synthetic method for the reduction of imines by samarium-induced reaction

IJC-B Vol.40B(11) [November 2001] p1134
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