Hydrochloric Acid → 3-(Dimethylamino)-6-phenoxy-1,2,3,4-tetrahydrocarbazole

HRID 128114Notes

Reaction equation

HRID 128114 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.Cl.[O:13]([C:20]1[CH:25]=[CH:24][C:23]([NH:26]N)=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:4][C:5]2[C:24]3[C:23](=[CH:22][CH:21]=[C:20]([O:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:25]=3)[NH:26][C:6]=2[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2760971(4-phenoxyphenyl)hydrazine HydrochlorideHCID 103745454-(Dimethylamino)cyclohexan-1-one

Product 1

HCID 123618043-(Dimethylamino)-6-phenoxy-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 14.1 g. of 4-dimethylaminocyclohexanone in 100 ml. of a 6-N solution of hydrogen chloride in absolute ethyl alcohol was added 23.5 g. of 4-phenoxyphenylhydrazine hydrochloride and the mixture was heated at reflux for six hours. The mixture was filtered, the filtrate was made alkaline with 10% potassium hydroxide and extracted with chloroform, and the chloroform extract was washed with water and evaporated to dryness under reduced pressure to give 3-(dimethylamino)-6-phenoxy-1,2,3,4-tetrahydrocarbazole.

Workup

  1. temperatureat reflux for six hours
  2. filtrationThe mixture was filtered
  3. extractionextracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with water
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8c213965f97a45da9d05d8be57358376
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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