Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1325769Notes

Reaction equation

HRID 1325769 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>COc1c(C(C)(C)C)cc(N2C=[N+](c3cc(C(C)(C)C)c(OC)c(C(C)(C)C)c3)[C@@H](c3ccccc3)[C@@H]2c2ccccc2)cc1C(C)(C)C.F[B-](F)(F)F.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O.COCCOCCOC.COCCOCCOC.COCCOCCOC.COCCOCCOC.COCCOCCOC>Cn1c(=O)c2c(ncn2C)n(C)c1=O.FC(F)(F)c1ccc(N2CCOCC2)cc1.FC(F)(F)c1cccc(N2CCOCC2)c1

Participants

9

Reactant 2

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

Product 3

HCID 2519CaffeineHCID 109333104-(4-Trifluoromethylphenyl)morpholineYield 3.16%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 4

HCID 2733832Lithium HexamethyldisilazideReagentHCID 178490099HCID 178490099, compoundCatalystHCID 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-933c710da3b1416985600080b870849b
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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