Sodium Bicarbonate → 1-(4-(Trifluoromethyl)phenyl)piperazine

HRID 1405427Notes

Reaction equation

HRID 1405427 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 23081333HCID 23081333, compound

Product 1

HCID 1217181-(4-(Trifluoromethyl)phenyl)piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
30 °C

Procedure

A solution of t-butyl 4-(4-(trifluoromethyl)phenyl)piperazine-1-carboxylate (1.06 g, 3.21 mmol, 1.00 equiv) in dichloromethane (10 mL) and trifluoroacetic acid (6 mL) was placed in a 50-mL round-bottom flask and stirred for 2 h at 30° C. in an oil bath. The pH value of the solution was adjusted to 7-8 with saturated aqueous sodium bicarbonate. The resulting solution was extracted with 4×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate, followed by filtration to remove the solids. The resulting solution was concentrated under vacuum, resulting in 740 mg (crude) of 1-(4-(trifluoromethyl)phenyl)piperazine as a yellow solid.

Workup

  1. extractionThe resulting solution was extracted with 4×30 mL of dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfollowed by filtration
  4. customto remove the solids
  5. concentrationThe resulting solution was concentrated under vacuum
  6. customresulting in 740 mg (crude) of 1-(4-(trifluoromethyl)phenyl)piperazine as a yellow solid

Sources & evidence

ORD record
ord-3370e21f1b0a4be8a232fa73725929a1
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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