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Piperidine → 1-(4-Methoxy-2-trifluoromethyl-phenyl)-piperidine

HRID 2100669
Notes
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Reaction equation

HRID 2100669 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].C(C1C=CC=C(C(C)C)C=1C1NC=C[N+]=1C1C(C(C)C)=CC=CC=1C(C)C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:3]([C:10]([F:13])([F:12])[F:11])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8082PiperidineHCID 144847271-Bromo-4-methoxy-2-(trifluoromethyl)benzeneHCID 68724604Di(2,6 diiso propylphenyl)imidazolium chloride

Product 1

HCID 688122121-(4-Methoxy-2-trifluoromethyl-phenyl)-piperidine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1-Bromo-4-methoxy-2-trifluoromethyl-benzene (500 mg, 1.961 mmol) in 1,4-dioxane (8 mL) is added sequentially: piperidine (2 eq., 3.921 mmol, 0.41 mL), Pd2dba3 (2 mol %, 0.039 mmol, 36 mg), KtOBu (1.5 eq., 2.941 mmol, 330 mg) and 1,3-(Bis(2,6-di-iso-propylphenyl)-imidazolium chloride (iPrHCl, 4 mol %, 0.078 mmol, 33 mg). The resulting reaction mixture is heated in a sealed tube at 150° C. oil bath for 12 hours. After cooling to room temperature, the reaction mixture is concentrated. The residue obtained is partially purified by silica gel chromatography (9:1 hexanes/EtOAc) to give crude 1-(4-Methoxy-2-trifluoromethyl-phenyl)-piperidine.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture is concentrated
  4. customThe residue obtained
  5. customis partially purified by silica gel chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ce421a24f2e64bda846ad57a65d0b82f
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572811B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes