Pyridine → 6-Benzyloxy-3-dimethlamino-1,2,3,4-tetrahydrocarbazole

HRID 863475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863475
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26]N)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C(O)C.O>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]2[C:23](=[CH:22][CH:21]=1)[NH:26][C:6]1[CH2:7][CH2:8][CH:3]([N:2]([CH3:10])[CH3:1])[CH2:4][C:5]2=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideHCID 103745454-(Dimethylamino)cyclohexan-1-one

Produkt 1

HCID 128917786-Benzyloxy-3-dimethlamino-1,2,3,4-tetrahydrocarbazoleAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 3.78 gm (26.8 mMol) 4-dimethylamino-1-cyclohexanone and 6.69 gm (26.8 mMol) 4-benzyloxyphenylhydrazine hydrochloride in 50 mL ethanol were added 2.17 mL (26.8 mMol) pyridine. To this solution were added 5×10 mL portions of water and the reaction mixture then stored at 0° C. for 18 hours. The reaction mixture was then diluted with an additional 50 mL of water and the mixture extracted well with dichloromethane. The combined organic extracts were dried over sodium sulfate and the volatiles removed under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with 9:1 chloroform:methanol. Fractions shown to contain the desired product were combined and concentrated under reduced pressure to give 2.14 gm (24.9%) of the title compound.

Aufarbeitung

  1. extractionthe mixture extracted well with dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customthe volatiles removed under reduced pressure
  4. washeluting with 9:1 chloroform
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eed351fb852b4036a5f91c2e5e4a373f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721252

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