Hydrochloric Acid → 3-(Dimethylamino)-6-fluoro-9-(4-fluorophenyl)-1,2,3,4-tetrahydrocarbazole

HRID 128135Notes

Reaction equation

HRID 128135 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)N)=[CH:14][CH:13]=1.Cl>C(O)C>[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][C:7]2[C:21]3[C:20](=[CH:25][CH:24]=[C:23]([F:26])[CH:22]=3)[N:18]([C:15]3[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=3)[C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 103745454-(Dimethylamino)cyclohexan-1-oneHCID 135657451,1-Bis(4-fluorophenyl)hydrazine

Product 1

HCID 128918083-(Dimethylamino)-6-fluoro-9-(4-fluorophenyl)-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 7.8 g. of 4-dimethylaminocyclohexanone and 11 g. of 1,1-bis(4-fluorophenyl)hydrazine in 350 ml. of absolute ethyl alcohol and 90 ml. of 5-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for five hours, cooled, and filtered. The solids were suspended in ether and treated with dilute sodium hydroxide solution and the ether extract was separated, dried and evaporated to dryness. The resulting oil was dissolved in ethyl alcohol, treated with hydrogen chloride in ethyl alcohol and the solution was concentrated and cooled. The resulting solids were collected by filtration to give, after recrystallization from ethyl alcohol, 5.6 g. of 3-(dimethylamino)-6-fluoro-9-(4-fluorophenyl)-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 283°-285° C.

Workup

  1. temperatureunder reflux for five hours
  2. temperaturecooled
  3. filtrationfiltered
  4. additiontreated with dilute sodium hydroxide solution
  5. extractionthe ether extract
  6. customwas separated
  7. customdried
  8. customevaporated to dryness
  9. dissolutionThe resulting oil was dissolved in ethyl alcohol
  10. additiontreated with hydrogen chloride in ethyl alcohol
  11. concentrationthe solution was concentrated
  12. temperaturecooled
  13. filtrationThe resulting solids were collected by filtration
  14. customto give
  15. customafter recrystallization from ethyl alcohol, 5.6 g

Sources & evidence

ORD record
ord-40059363bbb74793b922eeb04ff30b08
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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