p-Fluorophenethylamine → 5-Tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol

HRID 855247Notes

Reaction equation

HRID 855247 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:11]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([OH:23])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[BH4-].[Na+]>CO>[C:11]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:17]([OH:23])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 4653p-FluorophenethylamineHCID 4311764Sodium borohydrideHCID 137652724-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 693423465-Tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenolYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.83 g (13 mmol) of 2-(4-fluoro-phenyl) ethyl amine were added to 2.32 g (13 mmol) of 4-tert-butyl-2-hydroxy benzaldehyde dissolved in 130 ml methanol. The reaction mixture was stirred at rt over night under nitrogen. 492 mg (13 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 (250 g silica gel; DCM, then DCM/methanol 19:1) to yield 3.26 g (83%) of 5-tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol as a yellow viscous oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.24 (t, 2H), 7.09 (t, 2H), 6.95 (d, 1H), 6.71 (d, 1H), 6.68 (s, 1H), 3.76 (s, 2H), 1.23 (s, 9H).

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 (250 g silica gel

Sources & evidence

ORD record
ord-91137bb18f114c46b559d461d632ae07
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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