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Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1326574
Notes
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Reaction equation

HRID 1326574 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC(C)(C)[O-].COCCOCCOC.CS(C)=O.Clc1ccc(-n2cc[n+](-c3ccc(Cl)cc3)c2)cc1.[Cl-].[Cl][Cu].[Na+]>FC(F)(F)c1ccc(N2CCOCC2)cc1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

10

Reactant 2

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

Product 3

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

Reagents, catalysts & solvents 5

HCID 23676156Sodium t-butoxideReagentHCID 62652Cuprous chlorideCatalystHCID 159368781,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium 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-d578ca903c4b4880bbfd8ebb33405d20
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
DOI
10.1021/jacs.6c05959
Original link
View source

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes