Trifluoroacetic acid → 3,3-Bis(4-fluorophenyl)-1-(2-(piperazin-1-yl)ethyl)pyrrolidin-2-one

HRID 1667131Notes

Reaction equation

HRID 1667131 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[C:9]2=[O:28])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N(CC)CC)C>ClCCl>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:9]2=[O:28])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 67359885Tert-butyl 4-(2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)ethyl)piperazine-1-carboxylate

Product 1

HCID 674430113,3-Bis(4-fluorophenyl)-1-(2-(piperazin-1-yl)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 63B (2.00 g, 4.12 mmol) was dissolved in dichloromethane (40 mL) and treated with trifluoroacetic acid (7.40 g, 64.9 mmol) at 0° C. The reaction was allowed to come to room temperature and stirred for 1 hour. The reaction was neutralized with triethylamine and concentrated. The residue was taken into ethyl acetate, and then it was washed with water and brine, dried with MgSO4, filtered and concentrated to give the title compound. MS (DCI) m/z 386.2 (M+H)+.

Workup

  1. customto come to room temperature
  2. concentrationconcentrated
  3. washit was washed with water and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-008ab5481fc1483db7a204bdbd047ecb
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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