Acetone → [2-(4-Fluorophenyl)ethyl](propan-2-yl)amine

HRID 1351257Notes

Reaction equation

HRID 1351257 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1.[CH3:11][C:12]([CH3:14])=O.CO.C([BH3-])#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH:8][CH:12]([CH3:14])[CH3:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 4653p-FluorophenethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21098562[2-(4-Fluorophenyl)ethyl](propan-2-yl)amine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluorophenethylamine (1.4 g) in acetic acid (10 mL) was added dropwise acetone (0.82 mL) and methanol (20 mL). After sodium cyano-borohydride (0.64 g) was added, and the solution was stirred at room temperature for 2.5 hours. After adding water and diluting with ethyl acetate, the solution was washed with water and saturated sodium chloride water. After drying with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by NAM silica gel column chromatography (hexane/ethyl acetate), and the title compound (0.62 g) was obtained as colorless solids.

Workup

  1. washthe solution was washed with water and saturated sodium chloride water
  2. dry with materialAfter drying with anhydrous sodium sulfate
  3. customthe residue that was obtained
  4. customupon removing the solvent
  5. customby evaporation
  6. customwas purified by NAM silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7b3d68e78fb04411aa64ef3012cb2c39
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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