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

HRID 1077357Notes

Reaction equation

HRID 1077357 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 6 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 6 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-1ce19d5a290a40488da28062eaeabbf3
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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