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

HRID 1270369Notes

Reaction equation

HRID 1270369 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 and washed with saturated aqueous NaHCO3. The aqueous layer was extracted two more times with CH2Cl2. 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
  6. extractionThe aqueous layer was extracted two more times with CH2Cl2
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b5d13c6cf324ce197df3dc5454dcc18
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

Loading…