1-Chloro-4-(trifluoromethyl)benzene → 1-[4-(Trifluoromethyl)phenyl]piperidine

HRID 355560

Reaction equation

HRID 355560 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CC(C)([O-])C.[K+].[Br-].[Li+]>C1(C)C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:3][CH:4]=1.[F:9][C:8]([F:11])([F:10])[C:5]1[CH:4]=[C:3]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:2]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 8082PiperidineHCID 82050Lithium BromideHCID 23665647Potassium tert-butoxide

Product 2

HCID 4250921-[4-(Trifluoromethyl)phenyl]piperidineHCID 117702401-[3-(Trifluoromethyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In accordance with the GWI, 2.0 mmol of 4-chlorobenzotrifluoride, 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. 4-Trifluoromethylphenylpiperidine and 3-trifluoromethylphenylpiperidine in the ratio 6:1 are obtained in 65% yield.

Sources & evidence

ORD record
ord-a0215c4e20e2479e8ef59ab698c8bcbf
Source dataset
uspto-grants-1998_11
Patent number
US05831128

Linked notes

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