Tetrabutylammonium Fluoride → 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

HRID 1700380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700380
C([Si](CC)(CC)[C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][NH2:15])=[CH:10][C:9]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:7]=2)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:18][C:16]([F:17])([F:19])[C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][CH:4]=[C:12]2[CH2:13][CH2:14][NH2:15]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 120301422-[2-(Triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl]ethylamine

Produkt 1

HCID 120301362-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3.8 g of the compound obtained in Step C are stirred for 72 hours at ambient temperature in 200 ml of tetrahydrofuran and 10 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran in the presence of 1 g of 3 Å molecular sieve. After filtering off the resin and evaporating to dryness, the residue is taken up in 100 ml of 1N HCl and washed with dichloromethane. The aqueous phase is then rendered alkaline and extracted with dichloromethane and the combined organic phases are worked up in customary manner. The product obtained crystallises as the hydrochloride in an ethanol-diethyl ether-hydrogen chloride mixture.

Aufarbeitung

  1. filtrationAfter filtering off the resin
  2. customevaporating to dryness
  3. washwashed with dichloromethane
  4. extractionextracted with dichloromethane
  5. customThe product obtained
  6. customcrystallises as the hydrochloride in an ethanol-diethyl ether-hydrogen chloride mixture

Quellen und Nachweise

ORD-Eintrag
ord-bd2138c5de524aaaa69892de73911402
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350757B1

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