Trifluoroacetic acid → HCID 57803074, compound

HRID 2102682Notes

Reaction equation

HRID 2102682 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[C:29]3[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:31])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[Cl:30][C:26]1[CH:25]=[C:24]2[C:29]([C:21]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)[C:22](=[O:31])[NH:23]2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57803037HCID 57803037, compound

Product 1

HCID 57803074HCID 57803074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifloroacetic Acid (5 mL) was added to a solution of rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.24 g, 0.5 mmol) (from Example 12c supra) in dichloromethane (5 mL). The mixture was stirred at room temperature for 30 minutes. The solvent was evaporated in vacuo. To the residue was added saturated aqueous sodium bicarbonate solution, and extracted three times with ethyl acetate. The organic layers were combined, washed with water and brine, dried over Na2SO4 and concentrated to give rac-6-chloro-3-(3-chlorobenzyl)-3-piperidin-4-yl-1,3-dihydro-indol-2-one as a white solid. (Yield 0.18 g, 95%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo the residue was added saturated aqueous sodium bicarbonate solution
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-864b78f5b2ea4abd91e55411a91e8523
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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