Pyridine → 2,3,4,9-Tetrahydro-N,N-dimethyl-6-(phenylmethoxy)-1H-carbazol-3-amine

HRID 440941Notes

Reaction equation

HRID 440941 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 128917782,3,4,9-Tetrahydro-N,N-dimethyl-6-(phenylmethoxy)-1H-carbazol-3-amineYield 24.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-22bf537198b946f4a04fe433ffb43468
Source dataset
uspto-grants-1996_05
Patent number
US05521197

Reaction notes

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