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 1936708ノート

反応式

HRID 1936708 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-74365394984e413f8761ce14b4f09e0b
出典データセット
uspto-grants-2002_05
特許番号
US06391891B1

反応ノート

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