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Oxidative alpha-Amination of 4-methylpropiopnenone with Ammonium iodide

WillD

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Synthesis:
1. NH4I (15 g) was added to a mixture of sodium percarbonate (200 g), 4-methylpropiophenone (100 g), and methylamine (200 ml 40%) in DMF (600 ml) at room temperature.
2. The reaction was stirred at 50 *C 18 hours.
3. The reaction mixture was then allowed to cool to room temperature, dilute water (1500 ml).
4. Extracted with benzene (500 ml).
5. Acidified 5:1 solution conc. HCl in IPA to pH=5.
6. Crystallisation in cold 12 hours and filtered in vacuum, washing cold acetone and dry.
 
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ADATA

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This way directly 4MMC without bromination?
Are there any other alternatives to DMF?
acetone?
 

ADATA

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Are there any other options besides DMF?
 

WillD

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ADATA

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I will try the 4MMC harvested from this program
How much output can 1KG produce?
 

WillD

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For some reasons, the reaction poorly scale, start with a small scale
 

ADATA

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Is 1000G scale possible?
 

WillD

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Is 1000G scale possible?
ADATAMaybe, but start with smaller quantities. In general, the synthesis of the intermediate and its subsequent use is the best option than this synthesis.
 

karamelosanto

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Hi, I have a few questions about this route.
Methylamine 40% solution is in water or methanol ?
Can benzene be replaced with hexane or DCM or another solvent?
For scale this down like on the range of 10g 4-mpf. Is correct to scale down all the others reagents in the same 10/1 way?
Thanks
 

G.Patton

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zyuxo0

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Is this a good procedure to start my adventure with organic chemistry? Or should I start with classic halogenation?

I will do only nano scale. And I want to try because it looks like I can make a lot of experimental cathinones and this turns me on haha

What are the disadvantages of this procedure?

I know these are dumb questions for pros but anyways...
 

Mellym

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I guess this should work with carbamide peroxide (hydroperite) instead of sodium percarbonate.
Overall this scheme looks quite messy to me..
 

w2x3f5

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it is most likely better to use pre-prepared n-iodamine in this reaction
 

w2x3f5

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it is most likely better to use pre-prepared n-iodamine in this reaction
w2x3f5clarified, this makes no sense, since the reaction follows the path of halogenation and further amination. the reaction does not proceed through iodamine
 
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