Piperidine → 1-(4-Fluorophenyl)piperidine

HRID 355563Notes

Reaction equation

HRID 355563 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CC(C)([O-])C.[K+].[Br-].[Li+]>C1(C)C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:4]=1.[F:8][C:5]1[CH:4]=[C:3]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:2]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 9604Benzene, 1-chloro-4-fluoro-HCID 82050Lithium BromideHCID 23665647Potassium tert-butoxide

Product 2

HCID 108669271-(4-Fluorophenyl)piperidineHCID 10921100HCID 10921100, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 mmol of 4-chlorofluorobenzene, 2.4 mmol of piperidine, 2.8 mmol of potassium tert-butoxide, 0.4 mmol of lithium bromide, 1.0 mol-% (9.4 mg) of palladacycle (trans-di(μ-aceto)-bis[o[di-o-tolylphosphino)benzyl]dipalladium(II) in 10 ml of toluene are reacted according to the GWI to give 4-fluorophenylpiperidine and 3-fluorophenylpiperidine in the ratio 2:1 in 75% yield.

Sources & evidence

ORD record
ord-29dd7c87eeb74214955228b88959e0bd
Source dataset
uspto-grants-1998_11
Patent number
US05831128

Reaction notes

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