Trifluoroacetic acid → HCID 18689938, compound

HRID 1871922Notes

Reaction equation

HRID 1871922 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH:14]=[C:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18689933HCID 18689933, compound

Product 1

HCID 18689938HCID 18689938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonyl-4-(2-quinolylmethylene)piperidine (17.6 g) was dissolved in dichloromethane (60 ml), and TFA (60 ml) was added to the solution under cooling on ice. The mixture was stirred for 2.5 hours at room temperature and concentrated under reduced pressure. A saturated solution of sodium hydrogencarbonate was added to the residue to neutralize, and the mixture was then extracted with chloroform. The organic phase was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The title compound was recovered from an etherhexane solvent as white powder. This powder was also used for subsequent reaction without further purification.

Workup

  1. temperatureunder cooling on ice
  2. concentrationconcentrated under reduced pressure
  3. additionA saturated solution of sodium hydrogencarbonate was added to the residue
  4. extractionthe mixture was then extracted with chloroform
  5. dry with materialThe organic phase was dried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure
  7. customThe title compound was recovered from an etherhexane solvent as white powder
  8. customThis powder was also used for subsequent reaction without further purification

Sources & evidence

ORD record
ord-608e8741f1bb4b8bb7d3396782077e66
Source dataset
uspto-grants-2000_08
Patent number
US06107308

Reaction notes

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