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1-benzyl-1H-indole-3-carbaldehyde → HCID 10204285, Verbindung

HRID 2415127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2415127
Cl.Cl.[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:6]=1.C[O-].[Na+].[CH2:23]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH2:23]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:39][NH:19][CH2:18][CH2:17][CH2:16][NH:15][C:7]2[CH:6]=[C:5]([O:4][CH3:3])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 2621041-benzyl-1H-indole-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10942334Sodium MethoxideHCID 22640745HCID 22640745, Verbindung

Produkt 1

HCID 10204285HCID 10204285, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Katalysator
HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

A solution of N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (200 mg, 0.66 mmol) [4a] in methanol (50 ml) was treated with glacial acetic acid (20 drops) and sodium methoxide (95%, 71 mg, 1.31 mmol) followed by a solution of 1-benzyl-3-indole carboxaldehyde (155 mg, 0.66 mmol) in methanol (5.0 ml). The reaction stirred at ambient temperature for 24 hours then was treated with a solution of sodium cyanoborohydride (83 mg, 1.31 mmol) in methanol (2.0 ml). The reaction stirred at ambient temperature for 24 hours. The solution was evaporated under reduced pressure to a residue that was taken into a mixture of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide solution (20 ml). It was extracted in ethyl acetate and the extracts were dried (sodium sulfate) then concentrated to an oil. Column chromatography on silica (95/5 dichloromethane/methanolic ammonia) gave N-(1-benzyl-1H-indol-3-ylmethyl)-N′-(4-methoxyquinolin-2-yl)propane-1,3-diamine (126 mg, 84%) as a white solid. [M+H]+ 451.

Aufarbeitung

  1. stirringThe reaction stirred at ambient temperature for 24 hours
  2. customThe solution was evaporated under reduced pressure to a residue that
  3. additionwas taken into a mixture of saturated aqueous sodium chloride (20 ml) and 10% sodium hydroxide solution (20 ml)
  4. extractionIt was extracted in ethyl acetate
  5. dry with materialthe extracts were dried (sodium sulfate)
  6. concentrationthen concentrated to an oil

Quellen und Nachweise

ORD-Eintrag
ord-e412cdcb683e433ba12308c38f8ae7cc
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06818655B2

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