Methanesulfonic Acid → 3-(1-Piperidyl)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole

HRID 461560

Reaktionsgleichung

Reaktionsgleichung von HRID 461560
[N:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[NH:22]N.CS(O)(=O)=O>C(O)C>[N:1]1([CH:7]2[CH2:12][C:11]3[C:17]4[C:16](=[C:15]([F:14])[CH:20]=[C:19]([F:21])[CH:18]=4)[NH:22][C:10]=3[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 588958(2,4-Difluoro-phenyl)-hydrazineHCID 12361785Cyclohexanone, 4-(1-piperidinyl)-

Produkt 1

HCID 123618243-(1-Piperidyl)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 10.2 g. of 4-(1-piperidyl)-cyclohexanone, 8.1 g. of 2,4-difluorophenylhydrazine, and 11 g. of methanesulfonic acid in 100 ml. of absolute ethyl alcohol was heated under reflux for 12 hours, cooled, filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was treated in ether with 10% potassium hydroxide solution and the ether extract was washed with water, dried, and treated with hydrogen chloride in ethyl alcohol (excess HCl was avoided). The resulting gummy precipitate was separated by decantation and suspended in boiling isopropyl alcohol. The hot mixture was filtered to give, after recrystallization from absolute ethyl alcohol, 4.5 g. of 3-(1-piperidyl)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. > 290° C.

Aufarbeitung

  1. temperatureunder reflux for 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. additionThe residue was treated in ether with 10% potassium hydroxide solution
  6. extractionthe ether extract
  7. washwas washed with water
  8. customdried
  9. additiontreated with hydrogen chloride in ethyl alcohol (excess HCl was avoided)
  10. customThe resulting gummy precipitate was separated by decantation
  11. filtrationThe hot mixture was filtered
  12. customto give
  13. customafter recrystallization from absolute ethyl alcohol, 4.5 g

Quellen und Nachweise

ORD-Eintrag
ord-babb356db7d24e0ebcc7209ba8042f2f
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062864

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