Trifluoroacetic acid → HCID 59263044, compound

HRID 881029Notes

Reaction equation

HRID 881029 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:5][C:4]=1[F:26])#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[F:26][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:24]=[CH:25][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59263029Tert-butyl 4-[3-(4-cyano-3-fluorophenoxy)propyl]-1-piperidinecarboxylate

Product 1

HCID 59263044HCID 59263044, compoundYield 58.6%

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 g 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-248f59dd06f84fbdbe953ce6991efe3a
Source dataset
uspto-grants-2015_03
Patent number
US08993603B2

Reaction notes

Loading…