Potassium Carbonate → 2-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehyde

HRID 1678143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678143
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]=[O:17])=[C:8]2[N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([CH:26]1[O:28][CH2:27]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:28]1[CH2:27][CH:26]1[CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:8]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]3[C:10]([C:9]=2[CH:16]=[O:17])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 539968311-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde

Produkt 1

HCID 114852322-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehydeAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred mixture of 1-phenyl-2-(piperazin-1-yl)-1H-indole-3-carboxaldehyde (438 mg, 1.37 mmol), epibromohydrin (188 mg, 1.37 mmol), potassium carbonate (758 mg, 5.49 mmol) and acetonitrile (20 ml) is heated at reflux for 2.5 hr. The reaction is cooled and the solids are removed by filtration. The filtrate is concentrated and the residue is purified by chromatography eluting with dichloromethane-1 to 5% methanol. Fractions containing the desired product are combined and concentrated to afford 2-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehyde (41% yield) as a yellow solid. LC/MS: MS 376 (M+H); RT 2.65 min; NMR (CDCl3): 10.28 (1H, s), 8.26 (1H, d), 7.43-7.65 (3H, m), 7.17-7.42 (3H, m), 7.13 (1H, t), 6.96 (1H, d), 3.49 (4H, m), 3.03 (1H, m), 2.56-2.86 (4H, m), 2.30-2.50 (2H, m), 1.74 (2H, m), 1.56 (2H, s).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hr
  3. temperatureThe reaction is cooled
  4. customthe solids are removed by filtration
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by chromatography
  7. washeluting with dichloromethane-1 to 5% methanol
  8. additionFractions containing the desired product
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ebc7bca11a434806b3290dd610c2f33b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008491B2

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