Trifluoroacetic acid → 1-[2-Methoxy-4-(trifluoromethoxy)phenyl]piperazine

HRID 1058953Notes

Reaction equation

HRID 1058953 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:11]=1[N:21]1[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][C:17]([F:18])([F:19])[F:20])[CH:13]=[CH:12][C:11]=1[N:21]1[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 186690671,1-Dimethylethyl 4-[2-Methoxy-4-(trifluoromethoxy)phenyl]-1-piperazinecarboxylate

Product 1

HCID 186690731-[2-Methoxy-4-(trifluoromethoxy)phenyl]piperazineYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (90 mL) was added to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4-[2-methoxy-4-(trifluoromethoxy)phenyl]-1-piperazinecarboxylate (Description 17, 3.4 g) in dichloromethane (135 mL) and the mixture was stirred at room temperature for 1 h. The mixture was allowed to warm to room temperature, saturated aqueous sodium bicarbonate solution (380 mL) was added and the mixture was extracted with dichloromethane. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a pale brown solid (1.84 g, 74%). 1H NMR (250 MHz, CDCl3) δ3.28-3.58 (8H, m), 3.87 (3H, s), 6.77 (1H, d, J 1.9 Hz), 6.84 (1H, d, J 8.9 Hz), and 6.91-6.95 (1H, m).

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-37ebc774541e4be298ef039a463c1e6c
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

Loading…