Trifluoroacetic acid → 3,3-Bis(4-chlorophenyl)-1-(2-oxo-2-piperazin-1-ylethyl)pyrrolidin-2-one

HRID 2408855Notes

Reaction equation

HRID 2408855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[O:15])[C:9]2=[O:29])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](=[O:15])[N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:9]2=[O:29])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86657628tert-Butyl 4-(2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetyl)piperazine-1-carboxylate

Product 1

HCID 533901173,3-Bis(4-chlorophenyl)-1-(2-oxo-2-piperazin-1-ylethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 25E (0.920 g, 1.73 mmol) in CH2Cl2 (20 mL) was added trifluoroacetic acid (2.66 mL, 34.6 mmol) under nitrogen. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated to remove excess trifluoroacetic acid and then diluted with CH2Cl2 (150 ml). The organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine, dried with MgSO4, filtered, and concentrated. Purification by chromatography on silica gel, eluting with 7N NH3 in CH3OH/CH2Cl2, 3:97) yielded the title compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.42-7.30 (m, 8H), 4.16 (s, 2H), 3.40-3.29 (m, 7H), 2.75-2.59 (m, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove excess trifluoroacetic acid
  3. additiondiluted with CH2Cl2 (150 ml)
  4. washThe organic layer was washed with saturated aqueous NaHCO3 solution, water, and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography on silica gel
  9. washeluting with 7N NH3 in CH3OH/CH2Cl2, 3:97)

Sources & evidence

ORD record
ord-cede88c441d445569e5410f5d4630832
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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