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

HRID 1723825Notes

Reaction equation

HRID 1723825 reaction equation
[F:1][C:2]([F:25])([F:24])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:2]([F:1])([F:24])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68847847Tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine-1-carboxylate

Product 1

HCID 435103441-[4-(2,2,2-Trifluoroethoxy)phenyl]piperazineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine-1-carboxylate (32.47 g, approx 57 mmol) was dissolved in DCM (300 ml) and TFA (69 mL) was added. The reaction was stirred at room temperature overnight then evaporated to dryness, azeotroping with toluene. The residue was partitioned between DCM and saturated sodium bicarbonate solution. The organic phase was separated, dried (MgSO4), filtered and concentrated to yield 1-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine as a solid (13.48 g, 91%)

Workup

  1. customthen evaporated to dryness
  2. customazeotroping with toluene
  3. customThe residue was partitioned between DCM and saturated sodium bicarbonate solution
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4a7a68439a7489c929028d77cf10ea9
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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