Author Topic: 2,5-DMBA with Cyclohexylamine  (Read 746 times)

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  • Guest
2,5-DMBA with Cyclohexylamine
« on: July 04, 2004, 12:13:00 AM »
Does anyone know a recipe for 2,5-DMBA with cyclohexylamine ( AKA cyclohexanone ) ?

Molar ratios, yield, general procedure, even if brief, please.


  • Guest
For starters, cyclohexylamine IS not the same...
« Reply #1 on: July 04, 2004, 12:25:00 AM »
For starters, cyclohexylamine is not the same as cyclohexanone.

And if you use the search engine, I'm sure you'll find some information on this reaction, also look up the synthesis for mescaline in Pihkal. Shulgin uses cyclohexylamine as a catalyst in the formation of 3,4,5-TMNS. The same molar ratios, procedure etc could be used for 2,5-DMBA.

I'm not sure about yields,  but it should be somewhere around 75% I guess. According to

, EDDA seems to be a better choice when working with 2,5-DMBA with yields around 95%.


  • Guest
« Reply #2 on: July 04, 2004, 12:50:00 AM »
Sorry, I mean cyclohexanamine, my mistake.

I know about the EDDA recipe, but I would trade a slightly lower yield for having one less precursor to make.

Thanks for the info.


  • Guest
« Reply #3 on: July 04, 2004, 10:14:00 AM »
I know about the EDDA recipe, but I would trade a slightly lower yield for having one less precursor to make.

Taken from

A 150 ml beaker, containing 100 ml dry ether and 12.0 g (0.2 mol) of ethylenediamine, is placed in an ice-bath and a solution of 24.0 g (0.4 mol) glacial acetic acid in 20 ml ether is added with stirring at such a rate as to prevent boiling of the ether. The solution is left to crystallize overnight, then filtered with suction, the crystals washed with ether and recrystallized from approximately 50 ml MeOH. Yield after drying in a vacuum desiccator is around 27.5g (75%) of colorless needles, mp 114°C

First point, it is only a 2 days work to obtain plenty of catalyst. You should think ahead.

Second point, I wonder if it is really necessary to make EDDA in advance. For instance, the same document states that:

50 mmol of the substituted benzaldehyde, 60 mmol of nitroalkane and 5 mmol of ethylenediammonium diacetate is dissolved in 25-50 ml of iPrOH with stirring (with gentle heating if required to dissolve all solids) and the solution is left to stir at room temp for 24 h, whereafter the formed nitrostyrene is allowed to crystallize in the freezer for 12 h.

What if you follow this procedure with 50 mmol benzaldehyde, 60 mmol nitroalkane and 5 mmol ethylenediamine, dissolved in 25-50 mL iPrOH and 2 mL GAA? Is there a reason it shouldn't work, or does not give the same results?