Hydrochloric Acid → HCID 68564193, Verbindung

HRID 855197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855197
[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].Cl.[F:14][C:15]1[CH:16]=[C:17]([CH2:25][CH2:26][NH2:27])[CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:27][CH2:26][CH2:25][C:17]2[CH:18]=[CH:19][C:20]([C:21]([F:22])([F:23])[F:24])=[C:15]([F:14])[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydrideHCID 68696177875305-28-5

Produkt 1

HCID 68564193HCID 68564193, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1 ml of 4-tert-butylbenzaldehyde (6.16 mmol), 1 g of 2-(3-fluoro-4-trifluoromethyl-phenyl)-ethylamine hydrochloride (4.1 mmol) and 567 mg of potassium carbonate (4.1 mmol) were suspended in 12 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 3.5 h. After cooling down to rt, 233 mg (6.16 mmol) sodium borohydride were added and after stirring for 5 min at rt, the reaction mixture was then refluxed for 2.5 h. After cooling down to rt, the reaction mixture was treated with 0.8 ml 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 1:6 then 1:4) to give 1.156 g light yellow oil (79%). MS (ISP) 354.3 (M+H)+.

Aufarbeitung

  1. temperaturewere refluxed for 3.5 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 5 min at rt
  4. temperaturethe reaction mixture was then refluxed for 2.5 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

Quellen und Nachweise

ORD-Eintrag
ord-3cc7dc9edc60447da95b870a270c9408
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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