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

HRID 1666411Notes

Reaction equation

HRID 1666411 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=2)[CH:14]=[C:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[N:8][CH:9]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:30]=[CH:29][CH:28]=[C:13]([CH:14]=[C:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:12]=2)=[N:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66876086tert-Butyl 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 668759965-Ethoxy-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.46 mmol) in CH2Cl2 (5 mL) cooled to 0° C. under a N2 atmosphere was added TFA (1.1 mL, 14.6 mmol). The resulting mixture was stirred for 1 h at RT. The solution was concentrated and then quenched with saturated NaHCO3 solution. The mixture was extracted with CH2Cl2 and the organic layer was dried over Na2SO4, and concentrated under reduced pressure to give the title compound (0.45 g, 99%); m/z (311.5, M+ H+).

Workup

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

Sources & evidence

ORD record
ord-e97edbf7f913488e9739ad71ce2c5837
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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