Grrr... I am soo happy I found this thread.
For me, the paper from chemical warfare agent experimentators gupta et. al. (check their other papers on this compound) made good sense except the question why the N-nucleophile would accept the aldehyde over the ketone in the same molecule. But the said preferance of aldehydes over ketones (also shown in the papers of gribble and abd-el-magid in their famous STAB review articles) and the use of triethylamine as the helping base made swic stupid enough to aquire all chems in one of the countries where someone buying hydrogen peroxide will be directly accused of terrorism. OK, it´s not that bad, swic had most of it sitting on shelves except the 4-pip which he aquired silently and the STAB which he prepared by himself.
It took him three unsuccessful runs where he accused his sodium triacetoxyborohydride of being sodium di- or tertacetoxyborohydride (can that even be possible?) until the focus came on the piperidone polymerizing. Swic always smelled the phenylacetaldehyde in the end "product", a more or less sticky yellow to orange oil, with needles forming and dissolving again in acetone.
Swic really really wonders why the authors of the paper made the whole thing up.. on purpose .. or in the belief that it could work from the theory and then give a bad yield of 40% to make it more plausible.
So, jon, you suggest to reductively aminate the 4-piperidone with aniline first and then with the phenylacetaldehyde, right? Also by means of STAB?
That would be worth a try ..
And to finally answer the topic opener´s question: yes, you can substitute the DCE with THF, it does not matter.(no result anyway)
And to finally answer the topic opener´s question a second time: yes, you can substitute the DCE with THF, by giving the choice of these three solvents you show that you read all the important literature on reductive aminations with STAB and they say you can do so.
best regs
For me, the paper from chemical warfare agent experimentators gupta et. al. (check their other papers on this compound) made good sense except the question why the N-nucleophile would accept the aldehyde over the ketone in the same molecule. But the said preferance of aldehydes over ketones (also shown in the papers of gribble and abd-el-magid in their famous STAB review articles) and the use of triethylamine as the helping base made swic stupid enough to aquire all chems in one of the countries where someone buying hydrogen peroxide will be directly accused of terrorism. OK, it´s not that bad, swic had most of it sitting on shelves except the 4-pip which he aquired silently and the STAB which he prepared by himself.
It took him three unsuccessful runs where he accused his sodium triacetoxyborohydride of being sodium di- or tertacetoxyborohydride (can that even be possible?) until the focus came on the piperidone polymerizing. Swic always smelled the phenylacetaldehyde in the end "product", a more or less sticky yellow to orange oil, with needles forming and dissolving again in acetone.
Swic really really wonders why the authors of the paper made the whole thing up.. on purpose .. or in the belief that it could work from the theory and then give a bad yield of 40% to make it more plausible.
So, jon, you suggest to reductively aminate the 4-piperidone with aniline first and then with the phenylacetaldehyde, right? Also by means of STAB?
That would be worth a try ..
And to finally answer the topic opener´s question: yes, you can substitute the DCE with THF, it does not matter.(no result anyway)
And to finally answer the topic opener´s question a second time: yes, you can substitute the DCE with THF, by giving the choice of these three solvents you show that you read all the important literature on reductive aminations with STAB and they say you can do so.
best regs