Gamma-Aminobutyric Acid → 4-Amino-4'-methoxybutyrophenone trifluoromethanesulfonate

HRID 352062Notes

Reaction equation

HRID 352062 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O.[C:16]1([O:22][CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:19]1[CH:20]=[CH:21][C:16]([O:22][CH3:23])=[CH:17][CH:18]=1)=[O:15]

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 227150434-Amino-4'-methoxybutyrophenone trifluoromethanesulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Trifluoromethanesulfonic acid (4 ml) was ice-cooled, and 4-aminobutyric acid (1093 mg, 10.6 mmol) was added. Then, anisole (1 ml, 9.25 mmol) was added. The mixture was heated and stirred at 80° C. for 50 min. The mixture was cooled to room temperature and added dropwise to water (17 ml) under ice-cooling. The mixture was stirred under ice-cooling for 20 min and then at −10° C. for 30 min. The crystals were filtrated, washed with ice-cooled saturated brine, and dried under reduced pressure to give 4-amino-4′-methoxybutyrophenone trifluoromethanesulfonate (2.47 g, yield 78%).

Workup

  1. temperaturecooled
  2. temperatureThe mixture was heated
  3. temperatureThe mixture was cooled to room temperature
  4. temperaturecooling
  5. stirringThe mixture was stirred under ice-
  6. temperaturecooling for 20 min
  7. waitat −10° C. for 30 min
  8. filtrationThe crystals were filtrated
  9. washwashed with ice-
  10. temperaturecooled saturated brine
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-1b932d16f0c4403d881ba892628fa6e7
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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