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

HRID 1277470

반응식

HRID 1277470 반응식
[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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran3회HCID 24533Sodium amideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 737219H-Fluorene-9-carbonitrile

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ebd50d2e98944eb919a2d340d7d0254
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04277495

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