Hydrochloric Acid → N,5-Dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

HRID 427157노트

반응식

HRID 427157 반응식
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.O.C[NH:13][CH:14]1[CH2:26][C:25]2[C:24]3C(=CC(C)=CC=3)N[C:17]=2[CH2:16][CH2:15]1>C(O)C>[CH3:1][NH:2][CH:3]1[CH2:8][C:7]2[C:26]3[C:14](=[CH:15][CH:16]=[CH:17][C:25]=3[CH3:24])[NH:13][C:6]=2[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12361842N,7-Dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amineHCID 207606324-(Methylamino)cyclohexanone

생성물 1

HCID 12361843N,5-Dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of 15 g. of 4-methylaminocyclohexanone and 18.4 g. of 3-methylhydrazine hydrochloride in 200 ml. of absolute ethyl alcohol and 50 ml. of 4-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for six hours, cooled, and filtered to give 12.3 g. of solids which were slurried in 50 ml. of water. The slurry was cooled, the solids were collected by filtration, suspended in ether-chloroform, and the suspension was treated with dilute potassium hydroxide. The ether-chloroform extract was evaporated to dryness under pressure to give 7.6 g. of 3-(methylamino)-7-methyl-1,2,3,4-tetrahydrocarbazole, m.p. 163°-166° C. The alcoholic reaction mixture filtrate was evaporated to dryness under reduced pressure, the residue was boiled in isopropyl alcohol, and the insoluble material was collected by filtration, dissolved in water and the resulting solution was made alkaline with dilute potassium hydroxide. The resulting solids were collected by filtration to give, after recrystallization from ethyl acetate, 3.6 g. of 3-(methylamino)-5-methyl-1,2,3,4-tetrahydrocarbazole, m.p. 187°-190° C., which contained about 6% of the 7-methyl isomer as determined by gas chromatographic analysis.

후처리

  1. temperatureunder reflux for six hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customto give 12.3 g
  5. temperatureThe slurry was cooled
  6. filtrationthe solids were collected by filtration
  7. additionthe suspension was treated with dilute potassium hydroxide
  8. extractionThe ether-chloroform extract
  9. customwas evaporated to dryness under pressure
  10. customto give 7.6 g
  11. customThe alcoholic reaction mixture filtrate was evaporated to dryness under reduced pressure
  12. filtrationthe insoluble material was collected by filtration
  13. dissolutiondissolved in water
  14. filtrationThe resulting solids were collected by filtration
  15. customto give
  16. customafter recrystallization from ethyl acetate, 3.6 g

출처 및 근거

ORD 기록
ord-147bed0c93654d0685e922b0ea2404be
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04172834

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