Sodium borohydride → N-[2-[(5-Piperidinomethyl-2-furanyl)methylamino]ethyl]-2,3-dihydro-2-oxo-1H-benzimidazole

HRID 1461271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461271
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].[N:14]1([CH2:20][C:21]2[O:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[BH4-].[Na+]>C(O)C>[N:14]1([CH2:20][C:21]2[O:27][C:24]([CH2:25][NH:1][CH2:2][CH2:3][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[NH:6][C:5]3=[O:13])=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 117451761-(2-aminoethyl)-2,3-dihydro-2-oxo-1H-benzimidazoleHCID 156753865-(Piperidin-1-ylmethyl)furan-2-carbaldehyde

Produkt 1

HCID 10450804N-[2-[(5-Piperidinomethyl-2-furanyl)methylamino]ethyl]-2,3-dihydro-2-oxo-1H-benzimidazoleAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 100 ml of dry ethanol were dissolved 1.2 g (6.78 mmol) of Compound j and 1.3 g (6.78 mmol) of 5-piperidinomethylfurfural and the solution was stirred at room temperature for 20 hours. The reaction mixture was then cooled with ice and 1.18 g (31.1 mmol) of sodium borohydride was gradually added. The mixture was further stirred under ice-cooling for 1.5 hours. The reaction mixture was then concentrated, and after addition of methylene chloride, the resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. Finally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1) to give 1.26 g (52.9%) of Compound 18 as light yellow oil.

Aufarbeitung

  1. additionwas gradually added
  2. stirringThe mixture was further stirred under ice-
  3. temperaturecooling for 1.5 hours
  4. concentrationThe reaction mixture was then concentrated
  5. additionafter addition of methylene chloride
  6. washthe resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customFinally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-dfb4e838d16c4b598b337827b414810e
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075301

Notizen zur Reaktion

Wird geladen…