1-Methyl-4-piperidone → 1-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indole

HRID 1936708노트

반응식

HRID 1936708 반응식
[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C[O-].[Na+]>CO>[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[C:11]([C:20]4[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH:19]=4)=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 740491-Methyl-4-piperidoneHCID 104427751-Acetyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indoleHCID 10942334Sodium Methoxide

생성물 1

HCID 224625301-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indole수율 50.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred suspension of 1-acetyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indole (J. Med. Chem. 1995, 38, 2524) (1.60 g, 8 mmole) and 1-methylpiperidin-4-one (1.81 g, 16 mmole) in dry methanol (70 ml) was added sodium methoxide (2.59 g, 48 mmole). The mixture was heated at reflux under argon for 24 hours, then cooled and concentrated by evaporation to approx. 25% volume; then treated with water (5 ml), stirred and the solid precipatate collected by filtration. The solid was suspended in ethanol (20 ml), heated to boiling, cooled and filtered to leave the title compound as a pale cream powder (1.20 g).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 24 hours
  3. temperaturecooled
  4. concentrationconcentrated by evaporation to approx. 25% volume
  5. additionthen treated with water (5 ml)
  6. filtrationthe solid precipatate collected by filtration
  7. temperatureheated
  8. temperaturecooled
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-74365394984e413f8761ce14b4f09e0b
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391891B1

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