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Dresden's Chemical Fluff Thread (Name-A-Molecule)

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THORAZINE
1-(2-chlorophenothiazin-N-yl)-3-dimethylaminopropane

-antipsychotic (D2 antagonist)



RITALIN
1-phenyl-1-carbomethoxy-(2-piperidinyl)methane



AMPHETAMINE
2-amino-1-phenylpropane



ETHYLAMPHETAMINE
2-ethylamino-1-phenylpropane



N-carbomethoxy-1-phenyl-2-aminopropane



3,5-dicarbomethoxy-N-methylpiperidine
 
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The above compound is around x1239 morphine in animal models. The simpler models that only have a benzene pendant ring have a chiral methyl 1 carbon from benzene & the (S) isomer is about x300M.

I do appreciate that this isn't quite random fluff but it's fascinating how many of Lipinski's rules of 5 & how many of the 'morphine rules' it breaks. A salutary lesson that a piece of semi-science put forward by a senior Pfizer manager saw the entire company reject any an all compounds that broke the rule. It was only published in 1998, just as HTS was a big hit. Now I expect Pfizer to quietly be retesting all of the compounds binned simply for not following this 'rule' or, rather 'rule of thumb'.
 

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COVIDA_treatment

1-(2,5-dichloro-4-(1-thiabutyl)phenyl)-2-aminopropane

That Which Does Not Kill Us Makes Us Stronger



MUT
1-(2,5-dichloro-4-methylphenyl)-2-aminopropane
 
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wouldn't the acyl chloride in the precursor also react with the nitrogen in the piperidine ring to form amide?
For a start - then I suppose we can all guess where the HCl shows up? Indeed, why would the god of chemistry see fit to add just 1 meta acyl group? I suppose Levophacetoperane is the closest so maybe it's worth dredging through all that to discover that it doesn't offer any help at all.
 

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If 2-carboxypiperidine is added dropwise as the limiting reagent in a large excess of benzene, it won't be a problem.



MEREDITH
1-(4-methylphenyl)-1-(2-piperidinyl)methanone
 

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Better yet, use hypophophorous acid and avoid finicky halogens entirely!!!
 

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If 2-carboxypiperidine is added dropwise as the limiting reagent in a large excess of benzene, it won't be a problem.



MEREDITH
1-(4-methylphenyl)-1-(2-piperidinyl)methanone
Nope. Ann acyl chloride will bind to the basic N first and who is to say where else and how many other times will be an issue.

But by all means perform the reaction and supply lab notes.
 

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Thesis: Benzene plus hypophosphorus acid and 2-carboxypiperidine.
 

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MICHAEL
1-(5-methylthio-indole-3-yl)-2-aminopropane



FOD
1-methylamino-1-(2-fluorophenyl)cyclohexane



JUICE
4-hydroxybutanal
 
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VENMO
piperidin-4-yl 2,6-dimethylpyridin-4-yl ether



AWESOME_BLOSSOM
piperidin-4-yl 3,5-dimethoxypyridine-4-yl ether
 
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AARON
piperidin-4-yl 2,4,6-trichlorophenyl ether



MOSES
piperidin-4-yl 2,4,6-tribromophenyl ether



TASTY
racemic di reverse ester heroin
 
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CLAIRE
1-(4-chloro-2,6-dimethoxyphenyl)-2-aminopropane



SCUTUM
1-(5-chloroindole-3-yl)-2-aminopropane

Gone Get Down With Me.
Gone Get Down With Me.
Gone Make You Freak!
 
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WOODY 'DALTON' HARRELSON
Bk-1-oxo-N,N-diallyltryptamine



AMBER_GRIS
1-(2,4,6-trideuterophenyl)-2-aminopropane

If you glow in the dark, then you are radioactive!
 
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