Dimethylamine → 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

HRID 486224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486224
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][CH:15]2[C:27](=[O:28])[N:19]3[C:20]4[C:25]([CH:26]=[C:18]3[CH2:17][CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][NH:30][CH3:31].[CH2:32]=O>C(O)(=O)C>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH2:14][CH:15]2[C:27](=[O:28])[N:19]3[C:20]4[C:25]([C:26]([CH2:29][N:30]([CH3:32])[CH3:31])=[C:18]3[CH2:17][CH2:16]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 190973117-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Produkt 1

HCID 190973047-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (451 mg) in acetic acid (2.5 ml) at 10° C. were added successively aqueous 50% dimethylamine solution (0.17 ml) and aqueous 35% formaldehyde solution (0.16 ml). The mixture was heated at 60° C. for 16 hours. After evaporation of the solvent, the residue was dissolved in water, made basic with aqueous 3N sodium hydroxide solution, and extracted twice with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol-chloroform) to give 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-10-[(dimethylamino)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (233 mg) as an oil.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted twice with chloroform
  4. washThe chloroform layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (methanol-chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-97c0dcce96404826afb46ab5a8dc5d53
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290785

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