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

HRID 1666444Notes

Reaction equation

HRID 1666444 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]=[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[CH:4][C:3]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66875839tert-Butyl 4-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668754652-(2-Chloro-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridineYield 113.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (280 mg, 0.597 mmol) in CH2Cl2 (3 mL) cooled to 0° C. was added TFA (0.46 mL, 5.97 mmol). The resulting mixture was stirred for 2 h at RT. The reaction was concentrated and then partitioned between saturated NaHCO3 solution and CH2Cl2. The organic extract was dried over Na2SO4, and concentrated under reduced pressure to give the title compound (250 mg).

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between saturated NaHCO3 solution and CH2Cl2
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02e3161af27a4b65baf78c3b85f6c8ab
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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