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

HRID 1344738
Notes
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Reaction equation

HRID 1344738 reaction equation
c1ccc(C2CCNCC2)cc1.Ic1cccnc1>Cc1cc(O)cc(C)c1NC(=O)C(=O)Nc1c(C)cc(O)cc1C.C[Si](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
ParticipantsConditionsWorkupSources & evidenceReaction notes

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 8.663%

Reagents, catalysts & solvents 3

HCID 23672319Sodium trimethylsilanolateReagentHCID 126500385N1,N2-bis(4-hydroxy-2,6-dimethylphenyl)oxalamideCatalystHCID 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-3a606c866792419f962e48bc9a1a21ce
Source dataset
High-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
DOI
10.1021/jacs.6c05959
Original link
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Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes