Hydrogen Bromide → HCID 20145262, Verbindung

HRID 648638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648638
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:10]([CH:12]([CH:14]([C:24]([NH2:26])=[O:25])[C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH3:13])[CH:11]=1.[OH-].[Na+].[BrH:35]>O.[Cu]Br>[Br:35][C:6]1[CH:7]=[CH:8][C:9]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:10]([CH:12]([CH:14]([C:24]([NH2:26])=[O:25])[C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)[CH3:13])[CH:11]=1

Komponenten

7

Edukt 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 20145241HCID 20145241, VerbindungHCID 23668193Sodium Nitrite

Produkt 1

HCID 20145262HCID 20145262, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 0.072 gm (1.05 m mol) of sodium nitrite in 0.5 ml of water was added dropwise at an internal temperature of 0° to 5° C. to 0.40 gm (1.05 m mol) of 4-[(1-(5-amino-2-piperidino-phenyl)-ethyl)-aminocarbonylmethyl]-benzoic acid in 2 ml of semi-concentrated aqueous hydrobromic acid. The thus obtained diazonium salt solution was then added dropwise to 0.196 gm of copper-(I) bromide in 2 ml of 48% hydrobromic acid, whereby strong formation of gas occurred. The reaction mixture was stirred for 1.5 hours at an internal temperature of 45° to 50° C., cooled, and adjusted to pH 4 by means of 4N sodium hydroxide solution. After extraction with warm ethyl acetate, the extract was washed with water, dried, and filtered. After evaporation in vacuo, the residue obtained was purified by column chromatography on silica gel (chloroform/methanol=7:1).

Aufarbeitung

  1. temperaturecooled
  2. extractionAfter extraction with warm ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. filtrationfiltered
  6. customAfter evaporation in vacuo
  7. customthe residue obtained
  8. customwas purified by column chromatography on silica gel (chloroform/methanol=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-35d78875dcd5464793779c4b5b06333b
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04735959

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