Trifluoroacetic acid → 2-(3-(Phenyl(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate

HRID 1666482Notes

Reaction equation

HRID 1666482 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=3)[CH:22]=2)=[C:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[C:1]1([C:7](=[C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=2)[O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][N:29]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67445311tert-Butyl 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

Product 1

HCID 866239142-(3-(Phenyl(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate in CH2Cl2 (3 mL) was added trifluoroacetic acid (0.5 mL). The reaction was stirred overnight. The reaction was concentrated, redissolved in CH2Cl2 and concentrated again to give the title compound as an oil (33.7 mg, 70% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in CH2Cl2
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-4885579f4db146f69950e549ddf599bd
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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