4-Phenylpiperidine → 4-(4-Phenylpiperidin-1-yl)pyridine

HRID 1344083Notes

Reaction equation

HRID 1344083 reaction equation
Ic1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)[O-].CC(C)c1cccc(C(C)C)c1N1C=[N+](c2c(C(C)C)cccc2C(C)C)CC1.CC1=CC(C)=[O]->[Pd]2([O]1)[O]C(C)=CC(C)=[O]->2.CS(C)=O.[Cl-].[Na+]>c1ccc(C2CCN(c3cccnc3)CC2)cc1

Participants

9

Reactant 2

HCID 698734-PhenylpiperidineHCID 707143-Iodopyridine

Product 3

HCID 2519CaffeineHCID 1223802233-(4-Phenyl-1-piperidinyl)pyridineYield 0%HCID 1398883374-(4-Phenylpiperidin-1-yl)pyridineYield 27.947%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 27349181,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideCatalystHCID 178427257HCID 178427257, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

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-69655b202bbf415e86f6cac33b380e3a
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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