Trifluoroacetic acid → 3-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 2378625Notes

Reaction equation

HRID 2378625 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[CH:18]([CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10]1>ClCCl>[NH:22]1[CH2:21][CH2:20][CH:19]([CH:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:8])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59731916tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 183212463-(piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxylate (260 mg, 0.79 mmol) in dichloromethane (3 mL). Reaction stirred at room temperature for 1 hour. Reaction mixture was concentrated in vacuo. Residue was dissolved in methanol. Dowex 1×4-200 ion exchange resin was added to the mixture to create a slurry. Mixture stirred at room temperature for 30 minutes. Resin was filtered off and washed with methanol. Filtrate was concentrated. Title compound was obtained as dark foam in quantitative yield. MS m/e (M+H)+=231.1.

Workup

  1. customReaction
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionResidue was dissolved in methanol
  5. additionDowex 1×4-200 ion exchange resin was added to the mixture
  6. stirringMixture stirred at room temperature for 30 minutes
  7. filtrationResin was filtered off
  8. washwashed with methanol
  9. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-8e59d43ce48e4b21b5b0953e8170620b
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

Loading…