Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1325830Notes

Reaction equation

HRID 1325830 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC(=O)[O][Pd][O]C(C)=O.CC(C)(C)[O-].COCCOCCOC.CS(C)=O.[Cl-].[Na+].c1c[n+](C2CCCCC2)cn1C1CCCCC1>FC(F)(F)c1ccc(N2CCOCC2)cc1

Participants

10

Reactant 2

HCID 8083MorpholineHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 3

HCID 2519CaffeineHCID 109333104-(4-Trifluoromethylphenyl)morpholineYield 0.8%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 5

HCID 23676156Sodium t-butoxideReagentHCID 167845palladium(II) acetateCatalystHCID 109565421,3-DICYCLOHEXYL-IMIDAZOLIUM CHLORIDECatalystHCID 679Dimethyl SulfoxideSolvent5×HCID 8150DiglymeSolvent5×

Conditions

Temperature
60 °C

Workup

  1. customThe foil sealing tape was removed from the plate.
  2. addition3 μL of a 0.0667 M solution of caffeine in DMSO was added to each reaction well using an SPT Labtech Mosquito® liquid handling robot
  3. filtrationThe plates were then centrifuged for 15 to 20 seconds. · Keep liquid
  4. aliquotFollowing centrifugation, 500 nL of the resultant mixture from each well was carefully dispensed into four 384-well analytical plates (Analytical Sales # 38435) using an SPT Labtech Mosquito® liquid handling robot. Each well of these analytical plates contained 30 μL of DMSO with 0.1% acetic acid, pre-dosed by OpenTrons, to facilitate analysis.

Sources & evidence

ORD record
ord-64c9851e4b1143d0b40e8cfe8883edc7
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

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