p-Fluorophenethylamine → HCID 29558679, compound

HRID 855249Notes

Reaction equation

HRID 855249 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[F:11][C:12]([F:22])([F:21])[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:17][C:16]2[CH:15]=[CH:14][C:13]([C:12]([F:11])([F:21])[F:22])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4653p-FluorophenethylamineHCID 679964-(Trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 29558679HCID 29558679, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

562 mg (4 mmol) of 2-(4-fluoro-phenyl) ethyl amine were added to 733 mg (4 mmol) of 4-trifluoromethyl benzaldehyde dissolved in 40 ml methanol. The reaction mixture was stirred at rt over night under nitrogen. 151 mg (4 mmol) of sodium borohydride were added in portions and the reaction mixture was stirred for 2 h at rt. The solvent was evaporated and the residue was dissolved in DCM. The organic layer was washed with water and with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (60 g silica gel; DCM/methanol 19:1) to yield 1.16 g (98%) of [2-(4-fluoro-phenyl)-ethyl]-(4-trifluoromethyl-benzyl)-amine as a light yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.65 (d, 2H), 7.52 (d, 2H), 7.21 (dd, 2H), 7.06 (dd, 2H), 3.79 (s, 2H), 2.70 (s, 4H).

Workup

  1. stirringthe reaction mixture was stirred for 2 h at rt
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washThe organic layer was washed with water and with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography (60 g silica gel; DCM/methanol 19:1)

Sources & evidence

ORD record
ord-97d058f72a4e4656b8ff57d740a4cf18
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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