Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1328117Notes

Reaction equation

HRID 1328117 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>COCCOCCOC.CS(C)=O.C[Si](C)(C)[N-][Si](C)(C)C.Clc1ccc(-n2cc[n+](-c3ccc(Cl)cc3)c2)cc1.[Cl-].[Cu][I].[Li+]>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 7.32%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 5

HCID 2733832Lithium HexamethyldisilazideReagentHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 159368781,3-Bis(4-chlorophenyl)-1H-imidazol-3-ium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent5×HCID 8150DiglymeSolvent5×

Conditions

Temperature
30 °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-55285f52e4544d5691ed88c3f4a4bd89
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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