Trifluoroacetic acid → HCID 67147452, compound

HRID 2426082Notes

Reaction equation

HRID 2426082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14].FC(F)(F)C(O)=O>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58707252HCID 58707252, compound

Product 1

HCID 67147452HCID 67147452, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(3-(3,5-dichlorobenzylamino)-4-(methylsulfonyl)phenyl)-piperazine-1-carboxylate (0.5 mmol), trifluoroacetic acid (5 mL) and dichloromethane (10 mL) was stirred for 3 h and concentrated in vacuo. The residue was dissolved in dichloromethane; this solution was washed with aqueous NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo. The yellow solid residue was dissolved in dichloromethane (1 mL), reacted with 1 N HCl in ether (1 mL) and concentrated in vacuo to yield the title compound as a yellow solid (59%). 1H NMR (400 MHz, CDCl3): δ 9.37 (br, 1H), 7.62 (d, 1H), 7.28 (s, 1H), 7.22 (s, 2H), 6.24 (dd, 1H), 5.71 (d, 1H), 4.43 (d, 2H), 3.30 (m, 4H), 2.93 (m, 4H). MS (ESI) m/z: Calculated: 450.81; Observed: 415.4 (M+H+ corresponding to its free base).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthis solution was washed with aqueous NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe yellow solid residue was dissolved in dichloromethane (1 mL)
  7. customreacted with 1 N HCl in ether (1 mL)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e1a1cc7e185417e9d03cdd9c2c91a7a
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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