Trifluoroacetic acid → 6-(2-(piperazin-1-yl)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331294Notes

Reaction equation

HRID 331294 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:9]=2)[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:3]1[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[N:14]1([CH2:13][CH2:12][O:11][C:8]2[CH:9]=[C:10]3[C:5]([C:4]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:3]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[C:2]3=[O:1])=[CH:6][CH:7]=2)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 70312805tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylate

Product 1

HCID 510018316-(2-(piperazin-1-yl)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-(1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yloxy)ethyl)piperazine-1-carboxylate (0.38 mmol, 200 mg) obtained in Step 2 of Example 44 in CH2Cl2 (0.3M) was added TFA (20 eq). The resulting mixture was stirred at room temperature for 40 min and diluted with CH2Cl2. The solution was basicified to pH 9 by the addition of 3N NaOH. The mixture was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (acetone/hexanes=1:1) to obtain the title compound (75%).

Workup

  1. washThe mixture was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (acetone/hexanes=1:1)

Sources & evidence

ORD record
ord-d1edc047765948a3941283abebe1d577
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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