Tetrahydrofuran → 9-[3-(Dimethylamino)propyl]-9H-fluorene-9-carbonitrile

HRID 1262503

Reaktionsgleichung

Reaktionsgleichung von HRID 1262503
[NH2-].[Na+].O1CCCC1.[C:8]([CH:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)#[N:9].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl>O>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][C:10]1([C:8]#[N:9])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran3×HCID 24533Sodium amideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 737219H-Fluorene-9-carbonitrile

Produkt 1

HCID 129235709-[3-(Dimethylamino)propyl]-9H-fluorene-9-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 2.6 g. of sodium amide in 200 ml. of tetrahydrofuran was added dropwise over thirty minutes a solution of 12.7 g. of 9-cyanofluorene in 300 ml. of tetrahydrofuran. The reaction mixture was next heated to reflux for three hours, and then cooled to room temperature. While the reaction mixture was being stirred at room temperature, a solution of 14.2 g. of 3-dimethylaminopropyl chloride in 500 ml. of tetrahydrofuran was added dropwise over one hour. Following complete addition, the reaction mixture was again heated to reflux and stirred for sixteen hours. After cooling the mixture to room temperature, it was added to 500 ml. of water. The product was extracted into diethyl ether, and the ethereal extracts were combined, washed with water and dried. Removal of the solvent by evaporation under reduced pressure afforded, after distillation, 2.3 g. of 9-(3-dimethylaminopropyl)-9-cyanofluorene. B.P. 195°-201° C. at 0.1 torr.

Aufarbeitung

  1. temperatureThe reaction mixture was next heated
  2. temperatureto reflux for three hours
  3. additionaddition
  4. temperaturethe reaction mixture was again heated
  5. temperatureto reflux
  6. stirringstirred for sixteen hours
  7. temperatureAfter cooling the mixture to room temperature
  8. additionit was added to 500 ml
  9. extractionThe product was extracted into diethyl ether
  10. washwashed with water
  11. customdried
  12. customRemoval of the solvent
  13. customby evaporation under reduced pressure
  14. customafforded
  15. distillationafter distillation, 2.3 g

Quellen und Nachweise

ORD-Eintrag
ord-cd0433f8cbf845e68f2eb294c317d131
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04452745

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