Author Topic: Then there's the Zn/Ni-couple, Post 435995 .  (Read 2444 times)

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Then there's the Zn/Ni-couple, Post 435995 .
« on: October 14, 2004, 07:18:00 AM »
Then there's the Zn/Ni-couple,

Post 435995

(gabd: "Patent  FR971429", Chemistry Discourse)
. It can be used to aminate ketones with ammonia, but there is some secondary amines formed too.


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reduction test
« Reply #1 on: October 14, 2004, 11:51:00 AM »
2 grams Oxime was put together with 75 ml meoh and a huge amount of Nabh4 (0,75 grams). Great bubble evolution.
Hcl was added to maintain the ph 7-8.
After 1 hour the mixtur was processed ala Shulgin.
0,6 grams suspect pmoh freebase was solid in isopropanol and soluble in water also that is sure not the oxime.
Freebase was dissolved in DCM.
Isopropanol was saturated wit Citric acid, added to DCM.
DCM was evaporated in waterbad with vigorous stirring . A white precipitate was in the bottom of the flask.Propanol was poured of.
The white precipitate was rinsed with a small amount of water and recristallized from dH2O to give 0,5 grams white orange needles. Bioessay of this citrate will happen today evening 75 mg.


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« Reply #2 on: October 14, 2004, 07:10:00 PM »
75mg was tried without result.


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Try the Zinc Nh4Cl method!!..
« Reply #3 on: October 14, 2004, 08:33:00 PM »
It does work I've been using it on MDP2P and the resulting amine has been very happily active.

Using 1/3/2 molar ratio (oxime/nh4cl/zinc).

50ml methanol of solvent per 5g of oxime.
Run this for about 5 hours @ reflux stirring, making sure all the zinc is stirring or else it won't react, if you get bumping you aren't stirring well enough. I recommend a flat bottom flask for this task.


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« Reply #4 on: October 14, 2004, 08:54:00 PM »
Aluminium amalgam is better for me.
There is a lot of way to reduce the oxime.
The goal for me would be to reduce it with plain Gaa and Nabh4 to obtain the PMOH or MDOH. Nabh4 is clean, not dangerous easy to obtain and to use.
In Phikal Shulgin use the Cyano borohydride. With plain Nabh4 had to work too. The above posted reference (Gribble etc..) are a little to complicate for me, but I find this method could be reliable. The good old aluminium is calling me, bye.


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Reduction of O-Acyl Oximes with NaBH4/I2
« Reply #5 on: October 18, 2004, 04:09:00 AM »
Reduction of O-Acyl Oximes with Sodium Borohydride / Iodine System
Didier Barbry and Philippe Champagne

Synth. Commun. 25(22), 3503-3507 (1995)


O-acyl derivatives of aldoximes and ketoximes are reduced in good yields to the corresponding amines with sodium borohydride-iodine system.