Author Topic: 3,5-dimethoxy-4-trifluoromethylphenethylamine  (Read 2480 times)

0 Members and 1 Guest are viewing this topic.

Shambhala

  • Guest
3,5-dimethoxy-4-trifluoromethylphenethylamine
« on: July 13, 2000, 06:13:00 PM »
.


zooligan

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #1 on: July 14, 2000, 02:15:00 AM »

.


Truly enlightening.  It's all clear now.  Thanks!  I think this should definitely go in LaBTop's thread of detailed methods on the newbee board!



Shambhala

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #2 on: July 14, 2000, 08:02:00 PM »
Thank you,  you may now bow and kiss my ring.  I was going to explain to everyone how to make this stuff from table salt & playdough.  Then, I lost track of what I was doing  :P .  You bastard you, heh.  I was simply making an attempt to bring what I though an conversation(thread) from the couch to a place where it might be better off.   :P


Alphabeta121

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #3 on: July 18, 2000, 01:04:00 AM »
what about 2,5 dimethoxy 4-TFM PEA  ?



psyloxy

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #4 on: July 18, 2000, 01:18:00 AM »
Why are you always after the ultimate substance, with the ultimate potency ?
Yeah, it's cool but isn't it unreachable for most if not any of us ?

well, that's what I had to say on this...

--psyloxy--


foxy2

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #5 on: July 18, 2000, 01:23:00 AM »
Well there is no point in living if you don't have dreams.


"trip not equal to tryptamine, tryptamine equals trip"

Osmium

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #6 on: July 18, 2000, 12:31:00 PM »
Shame on you bees! Let's get busy and find the necessary refs to save this thread from becoming a farce!

Ok, this being said here is my contribution:

1,2,3-trimethoxybenzene ------> 1,3-dimethoxybenzene

Look at what Ugo Azzena et. al. have to say about it:

Synthesis 1; 1989; 28-30; / K, THF, RT, 24 hrs, 86%!

Tetrahedron Lett. 30; 13; 1989; 1689-90; / K, THF, RT, 24hrs

J. Org. Chem. 55; 19; 1990; 5386-5390; / K, THF, RT, 24hrs

Some other refs useful for this reaction:

J. Chem. Soc. Chem. Commun.; 1987; 1549-50 / K, THF, 87%, olivetol dimethyl ether also included, the one that started it all
J. Org. Chem. 57; 11; 1992; 3101-3106 Good one read it!

Chem. Ber. 44; 1911; 2135; / Na, EtOH; 1,2,3-trimethoxybenzene reduction

Synthesis 1990; 313-14;
1.) trimethoxybenzaldehyde dimethylacetal ---> 4-butyl-3,5-diMeO-benzaldehyde; Na, THF, RT, 53hrs, 86%!!!!
2.) trimethoxybenzaldehyde dimethylacetal ---> 4-ethyl-3,5-diMeO-benzaldehyde; Na, THF, 53hrs, RT, 75%
3.) trimethoxybenzaldehyde dimethylacetal ---> 3,5-dimethoxybenzaldehyde; Na, THF, 53hrs, RT, 92%

Recl. Trav. Chim. Pay-Bas, 109, 7/8; 1990, 443-445; / trimethoxybenzene ---> 1,3-dimethoxy-2-butylbenzene; BuLi, hexane

J. Org. Chem. 55; 19; 1990; 5386-5390; / trimethoxybenzene ---> (2,6-dimethoxyphenyl)trimethylsilane; 1) K, THF, RT, 24hrs; 2) THF, -50°C, 6hrs, chlorotrimethylsilane
Silicon containing psychedelics! We are the borgs and you will all be assimilated  ;)
Lots of useful shit in here (other metals, other electrophiles, substrates, regioselectivity, temp. dependence, product distributions). Get it and read it!

Chem. Ber. 41; 1908; 2556; / Na; EtOH; 5-allyl-1,2,3-trimethoxybenzene ---> 1,3-dimethoxy-5-propylbenzene

J. Chem. Soc. Perkin Trans 1; 3; 1995; 261-266
Tertrahedron Lett. 34; 35; 1993; 5635-38

And the special gift, ready for your favorite trifluoromethylation:

1,2,3-trimethoxybenzene -----> 2-iodo-1,3-dimethoxybenzene:
you guessed right, it another one of those Ugo Azzena refs listed above, the JOC 55 one.

1)K, THF, RT, 24hrs,
2) THF, -30°C, 2h, I2
 Same works with bromine @ -78°C

foxy2

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #7 on: July 18, 2000, 05:53:00 PM »
Good work, we should start a trust fund for the moderators.  They deserve it!!!!

"trip not equal to tryptamine, tryptamine equals trip"

Rhodium

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #8 on: July 18, 2000, 06:38:00 PM »
Foxy2: Yes we do. We should have an offshore bank account where our disciples could deposit any donations of excess assets  :)

Osmium: Is there any way one could fit a Me3Si- group in the 4-position of 2C-H? Is the Ar-SiMe3 group stable? The procedure above could only be used to make 3,5-MeO-4-TMS-PEA...

http://rhodium.lycaeum.org


Rhodium

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #9 on: July 20, 2000, 10:33:00 PM »
Hey Osmium, couldn't you answer this?

http://rhodium.lycaeum.org


Osmium

  • Guest
Re: 3,5-dimethoxy-4-trifluoromethylphenethylamine
« Reply #10 on: July 21, 2000, 12:34:00 PM »
Ok ok boss! But I want some of those new BORGAMINE/SILICAMINE designer drugs!  ;D ):

1,4-diMeO-benzene ---> 2,5-diMeO-phenyl-TMS: n-BuLi/TMEDA/Et2O/1hr/25°C/90%,(Tet. Lett. 36; 45; 1995; 8175-78)
1,2,4-triMeO-benzene:
TMEDA/BuLi/Et2O/hexane/RT/24hrs (Tetrahedron 47; 44; 1991; 9279-88 and JOC 49; 24; 1984; 4657-63)

1-Br-2,4,5-trimethoxybenzene:
J. Org. Chem. 49; 24; 1984; 4657-63 / n-BuLi/tert. amine/Et2O/0°C/1min

Interestingly enough, the TMS group can be removed from aromatics (good way to render a substance temporarily legal!  :P