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

HRID 461560

反応式

HRID 461560 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-babb356db7d24e0ebcc7209ba8042f2f
出典データセット
uspto-grants-1977_12
特許番号
US04062864

関連ノート

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