Reductive amination of aldehydes

Quote: Originally posted by getafix

such as piperonal with Al/Hg using 2-nitropropane as in situ amine source to create MDMA? Is this possible as a one-pot reaction?

Actually the reductive amination is performed with methylamine, which is generated in situ from nitromethane. Could this be where your confusion comes from?

Generally N-substituted amphetamines cannot be obtained directly from benzaldehyde and nitroalkane. You will have to either methylate the amphetamine (e.g. via formamide) or go via the phenylacetone and then reductively aminate with an amine.

In any case - MDMA can be had "on the streets". If I had piperonal, I would go for MDA.

[Edited on 5-12-2011 by turd]

Quote: Originally posted by zoombafu

Personally I would just stick to the experiment instructions, seeing as it is something that would in theory be taken orally. If you have little to no background in chemistry you shouldn't be messing around with stuff like this (in theory of course).

Quote: Originally posted by Sedit

Personally I would say stay away from trying to do what you are trying to do. You will either end up dead, in jail, or on the run. I have seen it over and over. Its no shock to anyone here that I value ones ability to make and use there own mind altering substances but I do have issues with those that have no interest in chemistry taking up this off shoot of the hobby. Go ahead it should work, reductively aminate BnO with Nitroethane. Just don't expect MDA for fuck sake. Know what the hell you are doing and you will stop giving people that like to experiment with there mind as much as they like to experiment with chemistry a bad name. People like you are more of my enemy then the DEA bitch!

Quote: Originally posted by turd

Quote: Originally posted by getafix   such as piperonal with Al/Hg using 2-nitropropane as in situ amine source to create MDMA? Is this possible as a one-pot reaction? This is not what is usually called "reductive amination". Reductive amination of an aldehyde is R-CHO + NH2 --> R-CH2-NH2 On piperonal this would yield 3,4-methylenedioxy-benzylamine. Not even close to what you want. The reaction you propose is a condensation with 2-nitropropane and reduction. Unfortunately this cannot work. If possible at all the condensation will stop at the beta-nitro-alcohol step: http://en.wikipedia.org/wiki/Nitroaldol_reaction Reduction of that would give an alpha,alpha-dimethyl-beta-hydroxy-phenethylamine (see phentermine, ephedrine). Certainly not what you want. Condensation with 1-nitropropane will also not yield MDMA, but the 4-carbon analogue of MDA (I think MDBD) Quote: Reductive amination of piperonal to MDA using nitroethane Al/Hg seems possible. Certainly possible, but that's not an reductive amination. Quote: Alternatively, can piperonal be condensed with 2-nitropropane (ammonium acetate, methylamine etc) to acquire a nitropene that can be reduced using Al/Hg approach to obtain MDMA? No. Quote: MDP2P can be created via piperonal and nitroethane (ammonium acetate condensation etc) to form the β-nitroisosafrole and then reacted with Fe/H+ to form MDP2P. Yes. Quote: MDMA then requires MDP2P being reductively aminated with nitromethane to yield MDMA but this means another couple of steps... Actually the reductive amination is performed with methylamine, which is generated in situ from nitromethane. Could this be where your confusion comes from? Generally N-substituted amphetamines cannot be obtained directly from benzaldehyde and nitroalkane. You will have to either methylate the amphetamine (e.g. via formamide) or go via the phenylacetone and then reductively aminate with an amine. In any case - MDMA can be had "on the streets". If I had piperonal, I would go for MDA. [Edited on 5-12-2011 by turd]

Good stuff turd!

I was wondering if it would mbdb but that is created using 1-nitropropane and results in the ethyl group. Does the same still apply for 2-nitropropane? If the condensation step is carried out first followed by a reduction?

I will have a closer look at the link you posted. Thank you very much.

Generally N-substituted amphetamines cannot be obtained directly from benzaldehyde and nitroalkane. You will have to either methylate the amphetamine (e.g. via formamide) or go via the phenylacetone and then reductively aminate with an amine.

This is what I was after I think.

Once piperonal is condensed with nitroethane the resultant nitrostyrene can be directly reduced to MDA looking at the structures. I was hoping the same might apply for piperonal condensed with the nitropropane and then followed by the reduction using Al/Hg.






[Edited on 5-12-2011 by getafix]

No means no! And I was wrong - it's called BDB: http://www.erowid.org/library/books_online/pihkal/pihkal094....
Before asking the same question again, tell us what you expect at the place of the three question marks in the following picture:

Quote: Originally posted by turd

Quote: Does the same still apply for 2-nitropropane? If the condensation step is carried out first followed by a reduction? No means no! And I was wrong - it's called BDB: http://www.erowid.org/library/books_online/pihkal/pihkal094.... Before asking the same question again, tell us what you expect at the place of the three question marks in the following picture:

Yes, I had come across BDB or J as the precursor to methyl-J or mbdb.

I was hoping it was going to be the corresponding nitrostyrene (nitropropene) that could be reduced to mdma using Al/Hg. I think I got confused by the condensation reaction involving nitromethane (as in 2CB synthesis) and the use of nitromethane during reductive amination of MDP2P. So thanks turd for your patience.

Nicodem: the very fact that nitropropane hadn't been used in mdma synthesis on any of the syntheses I have seen on Rhodium was a fairly big clue it wouldn't work. So I apologise if my attempt to make sense of why it wouldn't work upset you. Far better to live in ignorance apparently.

Anyway, I'm still smiling. Adios.

[Edited on 5-12-2011 by getafix]

Quote: Originally posted by turd

Quote: Does the same still apply for 2-nitropropane? If the condensation step is carried out first followed by a reduction? No means no! And I was wrong - it's called BDB: http://www.erowid.org/library/books_online/pihkal/pihkal094.... Before asking the same question again, tell us what you expect at the place of the three question marks in the following picture: