Trifluoroacetic acid → 1-(2-(3,5-Dichlorobenzylamino)-4-(piperazin-1-yl)phenyl)-2,2,2-trifluoroethanone hydrochloride

HRID 2426006Notes

Reaction equation

HRID 2426006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[CH:10]=[CH:11][C:12]=1[C:13](=[O:18])[C:14]([F:17])([F:16])[F:15].FC(F)(F)C(O)=O>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:10]=[CH:11][C:12]=1[C:13](=[O:18])[C:14]([F:16])([F:17])[F:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58707280t-Butyl 4-(3-(3,5-dichlorobenzylamino)-4-(2,2,2-trifluoroacetyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 866076581-(2-(3,5-Dichlorobenzylamino)-4-(piperazin-1-yl)phenyl)-2,2,2-trifluoroethanone hydrochlorideYield 136.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(3-(3,5-dichlorobenzylamino)-4-(2,2,2-trifluoroacetyl)phenyl)-piperazine-1-carboxylate (0.25 g, 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 compounds as a yellow solid (0.16 g, 73%). 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: 431; Observed: 432 (M+H+).

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-876c8aa925164415b874dceba20c0891
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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