Morpholine → 4-(4-Trifluoromethylphenyl)morpholine

HRID 1298823Notes

Reaction equation

HRID 1298823 reaction equation
C1COCCN1.FC(F)(F)c1ccc(Br)cc1>CC(C)(C)[O-].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.COCCOCCOC.COc1c(C(C)(C)C)cc(P(c2cc(C(C)(C)C)c(OC)c(C(C)(C)C)c2)c2ccc3c(c2-c2c(P(c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)ccc4c2OCO4)OCO3)cc1C(C)(C)C.[K+]>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 4.08%HCID 154202994-(3-(Trifluoromethyl)phenyl)morpholineYield 0%

Reagents, catalysts & solvents 4

HCID 23665647Potassium tert-butoxideReagentHCID 111941924,4'-Bi-1,3-benzodioxole-5,5'-diylbis{bis[4-methoxy-3,5-bis(2-methyl-2-propanyl)phenyl]phosphine}CatalystHCID 178440864HCID 178440864, compoundCatalystHCID 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-2eb3c06de3494e379ee1af1bdde1df86
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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