4-tert-Butylbenzaldehyde → (4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

HRID 639525

Reaktionsgleichung

Reaktionsgleichung von HRID 639525
[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].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 703244-tert-ButylbenzaldehydeHCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydride

Produkt 1

HCID 68560440(4-Tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amineAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-tert-butylbenzaldehyde (0.38 mL, 2.25 mmol) and 2-(3-trifluoromethyl-phenyl)-ethylamine (0.24 mL, 1.50 mmol) in methanol (4.5 mL) was stirred for 30 min at RT and subsequently refluxed for 4 h. After cooling, sodium borohydride (85 mg, 2.25 mmol) was added at RT, then after stirring for 5 min the reaction mixture was refluxed for 4 h. After cooling down to RT, the reaction mixture was treated with 1 M aq. hydrochloric acid solution (4 drops) and concentrated. The residue was dissolved in water/ethyl acetate. After separation of the organic phase, the aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with brine, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (SiO2; ethyl acetate/heptane 1:2) to afford the title compound (450 mg, 89%). Colorless viscous oil, MS (ISP) 336.3 (M+H)+.

Aufarbeitung

  1. temperaturesubsequently refluxed for 4 h
  2. temperatureAfter cooling
  3. temperaturewas refluxed for 4 h
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water/ethyl acetate
  6. customAfter separation of the organic phase
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washthe combined organic phases were washed with brine
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by column chromatography (SiO2; ethyl acetate/heptane 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-9269854498c24f8c98fbbf21390fe01f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691876B2

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