Trifluoroacetic acid → HCID 18695982, compound

HRID 618380Notes

Reaction equation

HRID 618380 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[N:16]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:15]2=[O:29])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:23][C:21]1[CH:20]=[CH:19][C:18]2[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:29])[N:16]([CH2:24][C:25]([F:27])([F:28])[F:26])[C:17]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 186959641-Tert-butoxycarbonyl-4-(5-fluoro-3-(2,2,2-trifluoroethyl)-2-oxo-1-benzimidazolinyl)piperidine

Product 1

HCID 18695982HCID 18695982, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-tert-butoxycarbonyl-4-(5-fluoro-3-(2,2,2-tri-fluoroethyl)-2-oxo-1-benzimidazolinyl)piperidine (4.17 g, 10 mmol.) in chloroform (50 mL) containing trifluoroacetic acid (5.5 mL) was stirred at room temp. under an inert atmosphere for 6-12 hours until reaction was complete. The solvent and excess TFA were removed and the residue redissolved in chloroform. This solution was washed with Na2CO3 /NaOH solution. The organic layer was dried (Na2SO4), filtered through a pad of charcoal, and the solvent evaporated to give 4-(5-fluoro-3-(2,2,2-trifluoroethyl)-2-oxo-1-benzimidazolinyl)piperidine as a viscous oil which was used as is. A sample of this material was converted to the HCl salt and after crystallization from methanol gave a white solid, mp: >280° C.

Workup

  1. customThe solvent and excess TFA were removed
  2. dissolutionthe residue redissolved in chloroform
  3. washThis solution was washed with Na2CO3 /NaOH solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered through a pad of charcoal
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-8669313a10214182a39d3bdcd67e8a7c
Source dataset
uspto-grants-1999_09
Patent number
US05952351

Reaction notes

Loading…