Trifluoroacetic acid → 3-(5-Bromo-2-fluorobenzyloxy)-1-(piperidin-2-yl)propane

HRID 1066814Notes

Reaction equation

HRID 1066814 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([CH:25]=1)[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:26])=[C:6]([CH:25]=1)[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 211960863-(5-Bromo-2-fluorobenzyloxy)-1-[1-(t-butoxycarbonyl)piperidin-2-yl]propane

Product 1

HCID 211959453-(5-Bromo-2-fluorobenzyloxy)-1-(piperidin-2-yl)propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(5-Bromo-2-fluorobenzyloxy)-1-[1-(t-butoxycarbonyl)piperidin-2-yl]propane (590 mg, 1.37 mmol) was dissolved in methylene chloride (11 ml), cooled to 0° C., and treated with 3 ml of trifluoroacetic acid. The reaction mixture was stirred at 0° C. for 20 minutes, then warmed to ambient temperature, and stirred an additional ten minutes. The reaction mixture was diluted with methylene chloride and quenched with saturated sodium bicarbonate. The pH was adjusted to about 10 with 1 N sodium hydroxide. The aqueous fraction was back-extracted with methylene chloride. The organic fractions were combined, dried over sodium sulfate, filtered, and concentrated.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred an additional ten minutes
  3. customquenched with saturated sodium bicarbonate
  4. extractionThe aqueous fraction was back-extracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3d7e761862f14dc19923d0f45e915d76
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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