05-24-03 11:00
No 435132
What's up folks!? Before I ask this question, I want to let you know that I don't really care if a psychedelic substituted compound is an amphetamine or a methylamphetamine; I love them either way.. With that in mind, I have a question about reductive amination.. In my dreams, I'm trying to decide which reductive amination I should use on a methylenedioxyphenylacetone; The Ammonium Chloride/Titanium(IV)Isopropoxide/Sodium
Love my country, fear my government.
(Chief Bee)
05-25-03 01:51
No 435274
It depends on your resources, if you can aquire Titanium(IV)Isopropoxide/Sodium Borohydride, then by all means use that method, as it uses less amine (nice if you are going the methylamine route), it can use any amine (imperative for MDA) and it also runs cooler, which means no fumes. It also is nicer to use on a small scale (<5g). On the other hand, the Al/Hg is cheaper and more OTC.
(Hive Addict)
05-25-03 09:06
No 435325
Like the ones barium and sunlight posted, SWIM is working on a CTH with Potassium Formate as the hydrogen source to reduce an imine swim will tell you how it goes when swim gets all the materials.
(PVC-Analog Taste-Tester)
05-25-03 10:22
No 435349
Thanks for the input, folks.
Love my country, fear my government.
(Hive Bee)
05-25-03 17:57
No 435421
Reductive Amination with good yield:
Patent DE865599:
(Chief Bee)
05-25-03 18:39
No 435426
Yes, but they are alkylating amphetamine with acetone and L-phenylacetylcarbinol (L-PAC) with cyclohexylamine, and the intermediate imines are much more stable than the ones gotten from phenyl-2-propanones and NH4Cl or CH3NH3Cl. You can see that the yield directly falls to sixty-something when using formaldehyde and a secondary amine. In addition to that they make use of Pt/H2 as reducing system, and that is much more cumbersome than either Al/Hg or NaBH4.
(Hive Bee)
05-26-03 00:23
No 435489
Yes, but i think, the idea of the patent was to use the amine as hydrochloride
roger2003
(Chief Bee)
05-26-03 00:29
No 435491
That is possible both in the Ti(iPrO)4/NaBH4 and Al/Hg reductive aminations too, you simply add one equivalent of base to deprotonate the salt.
(PVC-Analog Taste-Tester)
05-26-03 06:27
No 435530
I seem to remember a reference to increasing yields for the Al/Hg reductive amination by putting the reaction under pressure? Anyone know what the hell I'm talking about? Maybe a push-pull type of device could be rigged to it.
Just like with borohydrides, I'd prefer to store titanium(IV)isopropoxide in a freezer, surrounded by a larger container to keep out moisture.. Besides that, the only other downside to using Ti(iPrO)4/NaBH4 is that you need triethylamine, but that isn't watched..
Btw, I found a patent that involves Ti(iPrO)4/NaBH4; Patent US2001031498
"Various articles from Bhattacharyya et al. (J. Org. Chem., 1995, 60, pp. 4928-4929; Synlett, 1995, pp. 1079-1080; J. Chem. Soc., Perkin Trans. 1, 1998, pp. 2527-2531) have disclosed the process below for preparing amines from ketones or aldehydes, blah, blah"
Love my country, fear my government.
(BusyBee)
05-26-03 07:18
No 435546
One would think that PtO2 (Adam's Catalyst) would hypothetically work marvelously, with methylamine(g) (condensed to a liquid a suitably low temp) in MeOH (1/1/1 v/v/v) at 40 psi H2 for 1 hour
(PVC-Analog Taste-Tester)
05-26-03 07:22
No 435548
The thing that I'm not clear on is, after ammonium hydroxide's added to quench the Ti(iPrO)4/NaBH4 reaction mixture, can one just extract out the product amine, or does that triethylamine have to be distilled out first?
Love my country, fear my government.