Trifluoroacetic acid → HCID 59263044, compound

HRID 644121Notes

Reaction equation

HRID 644121 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14](C([O-])=O)[CH2:13][CH2:12]2)=[CH:5][C:4]=1[F:22])#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[F:22][C:4]1[CH:5]=[C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:20]=[CH:21][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86625836HCID 86625836, compound

Product 1

HCID 59263044HCID 59263044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (5.5 mL) solution of 0.66 g of tert-butyl=4-[3-(4-cyano-3-fluorophenoxy)propyl]-1-piperidinecarboxylate was dropwise added 1.8 mL of trifluoroacetic acid under cooling with ice over a period of 2 minutes, which was then stirred at room temperature for 6 hours. The solvent was distilled off under reduced pressure, and chloroform and a 1.0 mol/L sodium hydroxide aqueous solution were added to the resultant residue. The organic layer was separated and dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; chloroform:methanol=4:1) to provide 0.28 μg of 2-fluoro-4-[3-(4-piperidinyl)propoxy]benzonitrile as pale yellow oily form.

Workup

  1. temperatureunder cooling with ice over a period of 2 minutes
  2. distillationThe solvent was distilled off under reduced pressure, and chloroform
  3. additiona 1.0 mol/L sodium hydroxide aqueous solution were added to the resultant residue
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resultant residue was purified

Sources & evidence

ORD record
ord-3eaf37283e464e33957361c33d9cf7a9
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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