Trifluoroacetic acid → HCID 53814908, compound

HRID 582553Notes

Reaction equation

HRID 582553 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:15][O:16][CH3:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:15][O:16][CH3:17])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54110028HCID 54110028, compound

Product 1

HCID 53814908HCID 53814908, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(tert-butyloxycarbonyl)-1-[1-(4-fluorophenyl)-2-methoxyethyl]piperazine (1.46 g, 4.3 mmol) in CH2Cl2 (40 mL) was added trifluoroacetic acid (4 mL), and the mixture stirred at room temperature for 3 h. The solvent was evaporated and the residue azeotroped with toluene (2×20 mL). The residue was partitioned between EtOAc (2×50 mL) and Na2CO3 solution (sat., 50 mL). The combined organic phases were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (90:10:1), to afford the piperazine (0.95 g, 92%) as a pale yellow oil. 1H NMR (360 MHz, CDCl3) δ2.37-2.55 (4H, m), 2.86-2.89 (4H, m), 3.29 (3H, s), 3.45-3.48 (1H, m), 3.61 (1H, dd, J=9.9 and 5.2 Hz), 3.71 (1H, dd, J=9.9 and 5.8 Hz), 7.00 (2H, dd, JHA-HB =8.7 Hz and JHA-F =8.7 Hz), 7.27 (2H, dd, JHB-HA =8.7 Hz and JHB-F =5.6 Hz). MS (ES+) (239, M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue azeotroped with toluene (2×20 mL)
  3. customThe residue was partitioned between EtOAc (2×50 mL) and Na2CO3 solution (sat., 50 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with CH2Cl2 :MeOH:NH3 (90:10:1)

Sources & evidence

ORD record
ord-090510bc79a34ae9b6314c2213929448
Source dataset
uspto-grants-1999_07
Patent number
US05925638

Reaction notes

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