4-tert-Butylbenzylamine → (4-Tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amine

HRID 855176Notes

Reaction equation

HRID 855176 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:13][C:14]([F:20])([F:19])[CH2:15][CH2:16][CH:17]=O.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:17][CH2:16][CH2:15][C:14]([F:20])([F:19])[F:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 27770834,4,4-TrifluorobutanalHCID 4311764Sodium borohydride

Product 1

HCID 69342024(4-Tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amineYield 73.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.097 ml of 4-tert-butylbenzylamine (0.55 mmol) and 110 mg 4,4,4-trifluoro-butyraldehyde (0.83 mmol) were dissolved in 2 ml methanol and stirred 30 min at rt and then refluxed for 2.5 h. After cooling down to rt, 25 mg (0.66 mmol) of sodium borohydride were added and after stirring for 5 min at rt, the reaction mixture was refluxed for 2¾ h. After cooling down to rt, the reaction mixture was treated with 1 drop 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:2) to give 110 mg colorless viscous oil (73%). MS (ISP) 274.2 (M+H)+.

Workup

  1. temperaturerefluxed for 2.5 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 5 min at rt
  4. temperaturethe reaction mixture was refluxed for 2¾ h
  5. temperatureAfter cooling down to rt
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-4a26c1bf95134e38866be3d076a2454c
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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