Trifluoroacetic acid → 4-(Isoquinolin-4-yl)-4-hydroxypiperidine

HRID 1066072Notes

Reaction equation

HRID 1066072 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.[OH-].[Na+]>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][N:17]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 177895011-Tert-butoxycarbon-yl-4-(isoquinolin-4-yl)-4-hydroxypiperidine

Product 1

HCID 211980184-(Isoquinolin-4-yl)-4-hydroxypiperidineYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2.0 gm (6.1 mMol) 1-tert-butoxycarbon-yl-4-(isoquinolin-4-yl)-4-hydroxypiperidine, and 4 mL trifluoroacetic acid in 20 mL dichloromethane was stirred at room temperature for 18 hours. The reaction mixture was diluted with 2N sodium hydroxide and the phases were separated. The aqueous phase was extracted well with dichloromethane. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 10% to 40% methanol and a trace of ammonium hydroxide Fractions containing product were combined and concentrated under reduced pressure to provide 0.793 gm (57%) of the title compound as a light yellow solid.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted well with dichloromethane
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with dichloromethane containing from 10% to 40% methanol
  7. additiona trace of ammonium hydroxide Fractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a5aa0e7a2304755becf0b14de20bc93
Source dataset
uspto-grants-2001_06
Patent number
US06242450B1

Reaction notes

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