Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1319915Notes

Reaction equation

HRID 1319915 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC(C)(C)c1ccc(C=[CH](c2ccc(C(C)(C)C)cc2)->[Ni](<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)<-[CH](=Cc2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.CS(C)=O.CS(C)=O.Cc1cccc(C)c1.Cc1cccc(C)c1.Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.O=C([O-])[O-].[Cs+]>FC(F)(F)c1ccc(N2CCOCC2)cc1

Participants

11

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 6

HCID 14794698CID 14794698ReagentHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineCatalystHCID 178440864HCID 178440864, compoundCatalystHCID 679Dimethyl SulfoxideSolvent4×HCID 7929M-XyleneSolvent4×HCID 178504073HCID 178504073, compoundSolvent

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-b79303bbb9a349a1b2e31a0682ad4e9d
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
Original link
View source

Reaction notes

Loading…