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

HRID 1345449Notes

Reaction equation

HRID 1345449 reaction equation
c1ccc(C2CCNCC2)cc1.Ic1cccnc1>CC(C)(C)P(C(C)(C)C)c12->[Fe+2]3456789(<-c(c->3[cH-]->41)c->52)<-c1(-c2ccccc2)c->6(-c2ccccc2)c->7(-c2ccccc2)[c-]->8(-c2ccccc2)c->91-c1ccccc1.CC(C)(C)[O-].[Na+].CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O>Cn1c(=O)c2c(ncn2C)n(C)c1=O.c1ccc(C2CCN(c3cccnc3)CC2)cc1.c1ccc(C2CCN(c3ccncc3)CC2)cc1

Participants

8

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 18.234%

Reagents, catalysts & solvents 3

HCID 23676156Sodium t-butoxideReagentHCID 178454875HCID 178454875, compoundCatalystHCID 679Dimethyl SulfoxideSolvent5×

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-40b9840fd20d4e3caafc59a52b5bf301
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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