3-(4-Piperidinyl)-1H-indole → HCID 9908484, Verbindung

HRID 1532622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532622
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH:2]([OH:4])[CH2:3][N:15]1[CH2:20][CH2:19][CH:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:17][CH2:16]1)[CH:6]=[CH:7]2

Komponenten

3

Edukt 2

HCID 7022353-(4-Piperidinyl)-1H-indoleHCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indole

Produkt 1

HCID 9908484HCID 9908484, VerbindungAusbeute 51 %

Versuchsvorschrift

A methanolic solution of 1-N-glycidyl-5-fluoroindole (0.52 g, 3.0 mmole) from example 1 and 3-(4-piperidinyl)indole (0.6 g, 3.0 mmole) was refluxed under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford the titled compound as an oil (0.599 g, 50% yield). Treatment with a 0.25 M ethanolic solution of fumaric acid (0.5 equivalents) gave the required product as a white solid. The product was recrystallized twice from ethanol.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash silica gel chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-33fc7a89a3cf4adf8eb53404b405dc76
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204274B1

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