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Pyridine → 4-(4-Trifluoromethylphenoxy)piperidine-1-carbonylchloride

HRID 856139
Notes
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Reaction equation

HRID 856139 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[Cl:18][C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:19]([Cl:18])=[O:21])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidine

Product 1

HCID 202630804-(4-Trifluoromethylphenoxy)piperidine-1-carbonylchlorideYield 272.1%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

A mixture of 4-(4-trifluoromethylphenoxy) piperidine (0.6 g, 2.45 mmol), triphosgene (0.25 g, 0.86 mmol), and pyridine (0.4 ml, 4.90 mmol) in toluene (6 ml) was heated under reflux for 2.5 hours. To which ethyl acetate was added, and the mixture was washed with 10% hydrochloric acid, dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 4-(4-trifluoromethylphenoxy)piperidine-1-carbonylchloride (0.72 g, yield 96%) as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. washthe mixture was washed with 10% hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e740a24c81f4925b91b2aefd186d525
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes