Phenethylamine → (4-Tert-butyl-benzyl)-phenethyl-amine

HRID 855196Notes

Reaction equation

HRID 855196 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([NH2:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:21][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 4559933(4-Tert-butyl-benzyl)-phenethyl-amineYield 91.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.65 ml of 4-tert-butylbenzaldehyde (3.7 mmol) and 0.32 ml of phenethylamine (2.5 mmol) were dissolved in 7.5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2¼ h. After cooling down to rt, 142 mg (3.7 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was then refluxed for 3.5 h. After cooling down to rt, the reaction mixture was treated with 6 drops 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 (40 g silica gel; EtOAc/heptane 1:2) to give 609 mg of colorless oil (91%). MS (ISP) 268.3 (M+H)+.

Workup

  1. temperaturewere refluxed for 2¼ h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was then refluxed for 3.5 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 (40 g silica gel; EtOAc/heptane 1:2)

Sources & evidence

ORD record
ord-2100c4719ff4491f9f7ca0a098534bcc
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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