Trifluoroacetic acid → 2-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(2,2,2-trifluoroethoxy)pyridine

HRID 1666415Notes

Reaction equation

HRID 1666415 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=2)[CH:15]=[C:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[N:9][CH:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:19]1[CH2:20][CH2:21][C:16](=[CH:15][C:14]2[CH:13]=[C:12]([CH:31]=[CH:30][CH:29]=2)[O:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:33])([F:1])[F:32])=[CH:10][N:9]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66875845tert-Butyl 4-(3-(5-(2,2,2-trifluoroethoxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668761422-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(2,2,2-trifluoroethoxy)pyridineYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-(2,2,2-trifluoroethoxy)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.36 g, 0.77 mmol) in CH2Cl2 (3 mL) cooled to 0° C. under a N2 atmosphere was added TFA (0.46 mL, 5.97 mmol). The resulting mixture was stirred for 2 h at RT. The solution was concentrated and then quenched with saturated NaHCO3 solution. The mixture was extracted with CH2Cl2 and the organic extract was dried over Na2SO4, and concentrated under reduced pressure to give the title compound (0.282 g, 99%). m/z (365.1, M+ H+).

Workup

  1. concentrationThe solution was concentrated
  2. customquenched with saturated NaHCO3 solution
  3. extractionThe mixture was extracted with CH2Cl2
  4. extractionthe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ed8f9c775b34aa4bf2e2da3c626d3fa
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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