3-Fluorophenylhydrazine hydrochloride → 7-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

HRID 461557Notes

Reaction equation

HRID 461557 reaction equation
Cl.[CH3:2][N:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)[CH3:4].Cl.[F:13][C:14]1[CH:15]=[C:16]([NH:20]N)[CH:17]=[CH:18][CH:19]=1>C(O)C>[CH3:2][N:3]([CH3:4])[CH:5]1[CH2:10][C:9]2[C:17]3[C:16](=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)[NH:20][C:8]=2[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 23470418Dimethylaminocyclohexanone hydrochloride

Product 1

HCID 123618347-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 35.5 g. of dimethylaminocyclohexanone hydrochloride and 34.5 g. of 3-fluorophenylhydrazine hydrochloride in 500 ml. of absolute ethyl alcohol was heated at reflux for twenty hours and then cooled in an ice bath. The resulting crystals were collected by filtration, suspended in chloroform, and treated with dilute potassium hydroxide. The chloroform layer was separated and evaporated to dryness under reduced pressure to give, after recrystallization from isopropyl alcohol, 31.5 g. of 3-(dimethylamino)-7-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 174°-176° C.

Workup

  1. temperatureat reflux for twenty hours
  2. temperaturecooled in an ice bath
  3. filtrationThe resulting crystals were collected by filtration
  4. additiontreated with dilute potassium hydroxide
  5. customThe chloroform layer was separated
  6. customevaporated to dryness under reduced pressure
  7. customto give
  8. customafter recrystallization from isopropyl alcohol, 31.5 g

Sources & evidence

ORD record
ord-a9832ac93b5a4fdcafaa711afd387255
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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