Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1314898Notes

Reaction equation

HRID 1314898 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC1=CC(C)=[O]->[Ni]2([O]1)[O]C(C)=CC(C)=[O]->2.COCCOCCOC.C[Si](C)(C)[N-][Si](C)(C)C.Cc1cc(C)c([N+]2=CN(c3c(C(C)C)cccc3C(C)C)CC2)c(C)c1.[Cl-].[Na+]>FC(F)(F)c1ccc(N2CCOCC2)cc1

Participants

9

Reactant 2

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

Product 3

HCID 2519CaffeineHCID 109333104-(4-Trifluoromethylphenyl)morpholineYield 7.46%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 4

HCID 2724254Sodium bis(trimethylsilyl)amideReagentHCID 116179321-(2,6-Diisopropylphenyl)-3-(2,4,6-trimethylphenyl)-imidazolinium chlorideCatalystHCID 178427212HCID 178427212, compoundCatalystHCID 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-35cbbf0627254a08848bd85d12ef4123
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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