Benzaldehyde → 4-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide

HRID 344393

Reaktionsgleichung

Reaktionsgleichung von HRID 344393
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:20][CH2:19]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1.[BH4-].[Na+].O>C(O)C>[NH2:9][C:10]1[C:31]([Cl:32])=[CH:30][C:13]([C:14]([NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:22][CH2:23]2)=[O:15])=[C:12]([O:33][CH3:34])[CH:11]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

Produkt 1

HCID 540154964-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Benzaldehyde (0.76 g) was added to a solution of 4-amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide (2.0 g) in ethanol (50 ml), and the mixture was stirred at refluxing temperature for 3 hr. Sodium borohydride (0.53 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1) to give 1.78 g of 4-amino-N-((1-(5-benzylaminopentyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide.

Aufarbeitung

  1. temperatureat refluxing temperature for 3 hr
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia=50:5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d8d6108f1b35472588e42ea8e4f89e05
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

Verknüpfte Notizen

Wird geladen…