• N&PD Moderators: Skorpio | thegreenhand

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

 N-cyclopropyl-1-phenyl-1-oxo-2-aminopentane.png


NEW CAR SMELL
N-cyclopropyl-1-phenyl-1-oxo-2-aminopentane
 
  1-(2-chlorophenothiazin-N-yl)-3-dimethylaminopropane.png


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

-antipsychotic (D2 antagonist)

     1-phenyl-1-carbomethoxy-(2-piperidinyl)methane.png


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

    2-amino-1-phenylpropane.png


AMPHETAMINE
2-amino-1-phenylpropane

    2-ethylamino-1-phenylpropane.png


ETHYLAMPHETAMINE
2-ethylamino-1-phenylpropane

    N-carbomethoxy-1-phenyl-2-aminopropane.png


N-carbomethoxy-1-phenyl-2-aminopropane

     3,5-dicarbomethoxy-N-methylpiperidine.png


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'.
 


An oldie but a goody. I believe it was Fast&Bulbous who first suggested it BUT the only reference to it's synthesis in Reaxys was a mistake i.e. their is no paper describing the synh
 
1-(2,5-dichloro-4-(1-thiabutyl)phenyl)-2-aminopropane.png


COVIDA_treatment

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

That Which Does Not Kill Us Makes Us Stronger

   1-(2,5-dichloro-4-methylphenyl)-2-aminopropane.png


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

1-(4-methylphenyl)-1-(2-piperidinyl)methanone.png


MEREDITH
1-(4-methylphenyl)-1-(2-piperidinyl)methanone
 
Better yet, use hypophophorous acid and avoid finicky halogens entirely!!!
 
If 2-carboxypiperidine is added dropwise as the limiting reagent in a large excess of benzene, it won't be a problem.

1-(4-methylphenyl)-1-(2-piperidinyl)methanone.png


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.
 
Thesis: Benzene plus hypophosphorus acid and 2-carboxypiperidine.
 
  1-(5-methylthio-indole-3-yl)-2-aminopropane.png


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

1-methylamino-1-(2-fluorophenyl)cyclohexane.png


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

 4-hydroxybutanal.png


JUICE
4-hydroxybutanal
 
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 piperidin-4-yl 2,6-dimethylpyridin-4-yl ether.png


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

 piperidin-4-yl 3,5-dimethoxypyridine-4-yl ether.png


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


AARON
piperidin-4-yl 2,4,6-trichlorophenyl ether

  piperidin-4-yl 2,4,6-tribromophenyl ether.png


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

t3YbH6U.png


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


CLAIRE
1-(4-chloro-2,6-dimethoxyphenyl)-2-aminopropane

 1-(5-chloroindole-3-yl)-2-aminopropane.png


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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1-(indole-3-yl)-1-oxo-2-diallylaminoethane.png


WOODY 'DALTON' HARRELSON
Bk-1-oxo-N,N-diallyltryptamine

 1-(2,4,6-trideuterophenyl)-2-aminopropane.png


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

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