Trifluoroacetic acid → 1-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]piperazine

HRID 1723817Notes

Reaction equation

HRID 1723817 reaction equation
[F:1][C:2]([F:26])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:2]([F:1])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH:3]([F:4])[F:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86614576HCID 86614576, compound

Product 1

HCID 544321851-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]piperazineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude t-butyl 4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine-1-carboxylate (15.30 g, 0.04M) was dissolved in DCM (150 ml) and TFA (30 ml) was added. The mixture was stirred at room temperature overnight, evaporated to dryness and azeotroped with toluene. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution and the organic phase was collected, dried over MgSO4, filtered and evaporated to dryness to yield 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine as a solid (10.97 g, 98%)

Workup

  1. customevaporated to dryness
  2. customazeotroped with toluene
  3. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. customthe organic phase was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5f3cd80e3528442282c8bd9395496d01
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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