Trifluoroacetic acid → 2-(3-Cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

HRID 1666466Notes

Reaction equation

HRID 1666466 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=3)[CH:23]=2)[CH:7]=[C:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([C:4]2[CH:23]=[C:22]([CH:21]=[C:6]([CH:7]=[C:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[CH:5]=2)[O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][N:26]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66875428Tert-butyl 4-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668754182-(3-Cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 4-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.408 g, 0.859 mmol) in dry CH2Cl2 (5 mL) was added trifluoroacetic acid (1.0 mL, 13.05 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and at RT for 1 h. The reaction mixture was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2 three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (0.270 g, 84%) which was used in the next step.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2 three times
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-eab0a5b834bc432b8d0454433556ab83
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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