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Sodium Hydroxide → 2-((2-(1H-Indol-3-yl)ethyl)amino)ethanol

HRID 1199937
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199937
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][C:14](OCC)=[O:15])=[CH:2]1.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][CH2:14][OH:15])=[CH:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 14477069HCID 14477069, Verbindung

Produkt 1

HCID 123571312-((2-(1H-Indol-3-yl)ethyl)amino)ethanolAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

398 g of the product of Step A were dissolved in 4 liters of tetrahydrofuran cooled to +10° C. and while maintaining this temperature, 400 g of 25% sodium diethyl dihydroaluminate in toluene were introduced. The mixture was stirred for 90 minutes while allowing the temperture to rise to 17° C. The medium was cooled to -10° C. and 400 ml of sodium hydroxide solution in 1200 ml of water were introduced over 80 minutes while keeping the temperature at 0° C. during the introduction. The mixture was stirred for 2 hours at +10° C. then allowed to rise to ambient temperature for 16 hours with slower stirring. After decanting, the organic phase was washed with water and the wash water was extracted with ethyl acetate and methylene chloride. The combined organic phases were diluted with methylene chloride and dried, and the solvents were expelled at 40° C. under reduced pressure. The residue was triturated in 1300 ml of ethyl acetate for one hour, separated, washed with ethyl acetate and dried to obtain 240.8 g of the expected product melting at 92° C.

Aufarbeitung

  1. temperaturecooled to +10° C.
  2. additionwere introduced
  3. customto rise to 17° C
  4. customat 0° C.
  5. stirringThe mixture was stirred for 2 hours at +10° C.
  6. waitto rise to ambient temperature for 16 hours
  7. stirringwith slower stirring
  8. customAfter decanting
  9. washthe organic phase was washed with water
  10. extractionthe wash water was extracted with ethyl acetate and methylene chloride
  11. additionThe combined organic phases were diluted with methylene chloride
  12. customdried
  13. customwere expelled at 40° C. under reduced pressure
  14. customThe residue was triturated in 1300 ml of ethyl acetate for one hour
  15. customseparated
  16. washwashed with ethyl acetate
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-638f223778ee479590ea575c71e078fd
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04904655

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