Trifluoroacetic acid → 1'-(2,2,2-Trifluoroethyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1921182Notes

Reaction equation

HRID 1921182 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:3][CH2:2]1.[F:16][C:17]([F:22])([F:21])[C:18](O)=O.FC(F)(F)S(OCC(F)(F)F)(=O)=O.C(N(CC)CC)C>CC(C)=O>[F:16][C:17]([F:22])([F:21])[CH2:18][N:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 18435788Spiro(indole-3,4'-piperidin)-2(1H)-one

Product 1

HCID 184493581'-(2,2,2-Trifluoroethyl)-spiro[indoline-3,4'-piperidin]-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of spiro[indoline-3,4′-piperidin]-2-one, [PCT Int. Appl. WO 0145707 A1 (2001)] trifluoroacetic acid salt (3.66 g, 11.6 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.63 mL, 11.6 mmol), and triethylamine (8.06 mL, 57.9 mmol) in acetone (30 mL) was heated at reflux for 16 h. The mixture was allowed to cool, and the solvent removed under reduced pressure. The residue was taken up in CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was further extracted with CH2Cl2 (2×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=285 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureto cool
  4. customthe solvent removed under reduced pressure
  5. washwashed with saturated aqueous NaHCO3 (50 mL)
  6. extractionThe aqueous layer was further extracted with CH2Cl2 (2×25 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54825f58bf794b1d9a186ccccbf68fc7
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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