3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole → 5-Methoxy-3-(piperidin-4-yl)-1H-indole

HRID 1252054노트

반응식

HRID 1252054 반응식
C([N:4]1[CH:9]=[CH:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][CH:11]=2)[CH:6]=[CH:5]1)(=O)C.C(N1CCC(C2C3C(=CC=C(OC)C=3)NC=2)CC1)(=O)C>C(O)C.O=[Pt]=O.[OH-].[Na+]>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

참가 물질

6

반응물 2

HCID 149317413-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindoleHCID 201409353-(1-Acetyl-4-piperidyl)-5-methoxyindole

생성물 1

HCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indole수율 74.6%

시약·촉매·용매 3

HCID 345198Adams' catalyst촉매HCID 702Ethanol용매2회HCID 14798Sodium Hydroxide용매

실험 절차

3-(1-Acetyl-1,4-dihydro-4-pyridyl)-5-methoxyindole (3.0 g) was dissolved in hot ethanol (150 ml) and hydrogenation was carried out with Adams catalyst (0.25 g). The mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue containing 3-(1-acetyl-4-piperidyl)-5-methoxyindole. This residue was diluted with 2N aqueous sodium hydroxide solution (22 ml) and ethanol (30 ml) and refluxed for 18 hours. Ethanol was then distilled off and the residue was cooled. The precipitate was collected by filtration and recrystallized from a mixture of ethanol and water to give 5-methoxy-3-(4piperidyl)indole (1.92 g).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue
  4. temperaturerefluxed for 18 hours
  5. distillationEthanol was then distilled off
  6. temperaturethe residue was cooled
  7. filtrationThe precipitate was collected by filtration
  8. customrecrystallized from a mixture of ethanol and water

출처 및 근거

ORD 기록
ord-78cb878c446b42b484b0c8d4d514b6cc
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04742057

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