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

HRID 1343995Notes

Reaction equation

HRID 1343995 reaction equation
Ic1cccnc1.c1ccc(C2CCNCC2)cc1>CC(C)(C)[O-].CS(C)=O.[Cl-].[Cu][Br].[Na+].c1c[n+](C2CCCCC2)cn1C1CCCCC1>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 8.866%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 24593copper(I) bromideCatalystHCID 109565421,3-DICYCLOHEXYL-IMIDAZOLIUM CHLORIDECatalystHCID 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-f1a452bb825749f5bf2f1e2e56d8c152
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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