Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Help me synthesize an interesting molecule
chemStudent9000
Harmless
*




Posts: 3
Registered: 8-2-2016
Member Is Offline

Mood: No Mood

shocked.gif posted on 8-2-2016 at 15:15
Help me synthesize an interesting molecule


I am an organic chemistry student and in lab we have performed the attached synthesis to form 2,3-Dihydro-2,2,4-trimethyl-1H-1,5-benzodiazepine ImagesHandler.ashx.png - 7kB. I can probably provide the paper with the entire mechanism if anyone is interested.

Having performed this synthesis our next task is to come up with an idea for another molecule. This new molecule can be synthesized from the above benzo product or we can alter the original synthesis in some way to get this new molecule.

The reason I am posting here is to see if anyone has any ideas on what I should synthesize. I assume most other students will make some random change to their starting reactants to yield some molecule with little thought to their final product.

I would like to synthesize something interesting but I lack the chemistry knowledge to come up with much on my own. Are their any chemistry resources out their were I can search for molecules with similar structure to the on above and get ideas for the new synthesis?


synth.PNG - 4kB

[Edited on 9-2-2016 by chemStudent9000]
View user's profile View All Posts By User
Neuro-
Harmless
*




Posts: 29
Registered: 24-1-2016
Member Is Offline

Mood: No Mood

[*] posted on 8-2-2016 at 16:42


Well benzodiazepines are some of the most studied compounds ever (top selling, been around for decades. You could easily find resources on places like rhodium due to the fact most benzo's are drugs, and there are a number of syntheses you could attempt https://www.erowid.org/archive/rhodium/chemistry/diazepam.ht... You might not want to make scheduled substances (prison wouldn't be fun) but you could simply not substitute the wrong things in the right place (search the Markush structure). I'd love to see the paper, I've been looking for a way to try benzodiazepine synthesis without the legal problem of making a scheduled substance. Personally making basic ring structure of midazolam without the attached phenol ring and the halogens would be a cool exercise.

[Edited on 9-2-2016 by Neuro-]
View user's profile View All Posts By User
chemStudent9000
Harmless
*




Posts: 3
Registered: 8-2-2016
Member Is Offline

Mood: No Mood

[*] posted on 8-2-2016 at 17:16


Thanks for the input Neuro, especially with the idea of searching for the Markush structure. I've attached the paper for anyone interested. I would love to hear what ideas other people have.

Attachment: benzodiazepine supplemental information-1.docx (2.1MB)
This file has been downloaded 1641 times

Attachment: benzodiazepine.pdf (73kB)
This file has been downloaded 319 times

View user's profile View All Posts By User
AvBaeyer
International Hazard
*****




Posts: 580
Registered: 25-2-2014
Location: CA
Member Is Offline

Mood: No Mood

[*] posted on 8-2-2016 at 20:21


You might consider using ethylenediamine in place of the o-phenylenediamine. This could produce a diazepine instead of the benzodiazepine. The sterics of the reaction would be considerably altered and could lead to an interesting discussion based on whatever products you might find.

AvB
View user's profile View All Posts By User
CuReUS
International Hazard
*****




Posts: 928
Registered: 9-9-2014
Member Is Offline

Mood: No Mood

[*] posted on 9-2-2016 at 05:07


I don't know much about benzodiazepines ,so I don't know which are legal and which are not,so you have to check that out
a few things you could do would be to halogenate or hydroxylate the phenyl ring,alkylate the secondary amine or use halogenated ketones rather than a plain one.(the logic being since trichloroacetaldehyde is a sedative,and benzodiazepines are also used as sedatives,something should happen ;)) .maybe you could use dibenzylketone or even dibenzylidene acetone and cause furthur resonance :D
View user's profile View All Posts By User
chemStudent9000
Harmless
*




Posts: 3
Registered: 8-2-2016
Member Is Offline

Mood: No Mood

[*] posted on 9-2-2016 at 12:57


These are all great ideas, I'll have to think about what I want to do. I'll be sure to post back here and let everyone know what I come up with.
View user's profile View All Posts By User

  Go To Top