Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1311387Notes

Reaction equation

HRID 1311387 reaction equation
C1COCCN1.FC(F)(F)c1ccc(I)cc1>CC1=CC(C)=[O]->[Cu]2([O]1)[O]C(C)=CC(C)=[O]->2.CNc1ccc2ccccc2c1-c1c(NC)ccc2ccccc12.CS(C)=O.C[Si](C)(C)[O-].[Na+]>FC(F)(F)c1ccc(N2CCOCC2)cc1

Participants

9

Reactant 2

HCID 8083MorpholineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-

Product 3

HCID 2519CaffeineHCID 109333104-(4-Trifluoromethylphenyl)morpholineYield 0.51%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 4

HCID 23672319Sodium trimethylsilanolateReagentHCID 628556(R)-N,Nμ-Dimethyl-2,2μ-diamino-1,1μ-binaphthyl, (R)-N,Nμ-Dimethyl-1,1μ-binaphthalene-2,2μ-diamineCatalystHCID 178426894HCID 178426894, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

Conditions

Temperature
80 °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-bdda00eea43c4e69a7834ec9c404b581
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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