Trifluoroacetic acid → HCID 18689939, compound

HRID 1871925Notes

Reaction equation

HRID 1871925 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH: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[CH2:14][C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18689930HCID 18689930, compound

Product 1

HCID 18689939HCID 18689939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonyl-4-(2-quinolylmethyl)-1,2,5,6-tetrahydropyridine (1.98 g) was dissolved in dichloromethane (5 ml), and TFA (5 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, 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 ether-hexane 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 ether-hexane solvent as white powder
  8. customThis powder was also used for subsequent reaction without further purification

Sources & evidence

ORD record
ord-45cb6f3a94fc4d02bb78919c53688a96
Source dataset
uspto-grants-2000_08
Patent number
US06107308

Reaction notes

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