Piperidine → (E)-3-(5-Nitroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 618104

Reaktionsgleichung

Reaktionsgleichung von HRID 618104
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH:28]=O)([O-:18])=[O:17].N1CCCCC1>CN(C)C=O>[N+:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2/[CH:28]=[CH:14]/[C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15])([O-:18])=[O:17]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 143453',4',5'-TrimethoxyacetophenoneHCID 2460395-nitro-1H-indole-3-carbaldehyde

Produkt 1

HCID 21850180(E)-3-(5-Nitroindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneAusbeute 5,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3',4',5'-Trimethoxyacetophenone (1.31 g) and 5-nitroindole-3-carboxaldehyde (1.18 g) were dissolved in N,N-dimethylformamide (20 ml), and piperidine (528.7 mg) was added thereto, followed by stirring at 100° C. for 72 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from methanol to give Compound 21 (125 mg).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. customThe obtained crude crystals
  4. customwere recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-e5fc7ad1fae14f72a4885117db483730
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952355

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