Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 34900

Reaktionsgleichung

Reaktionsgleichung von HRID 34900
C1(=O)N([N:6]2[CH:14]=[CH:13][CH:12]=[C:8]([C:9]([O-:11])=O)[CH2:7]2)C(=O)CC1.[CH2:17]([CH2:19][NH2:20])[OH:18].C(N(C(C)C)CC)(C)C.C(N)C.CN(C=O)C.C([O-])(=O)C1C=CC=NC=1.ON1C(=O)CCC1=O>CN(C=O)C>[OH:18][CH2:17][CH2:19][NH:20][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[N:6][CH:7]=1

Komponenten

8

Edukt 6

HCID 700Ethanolamine2×HCID 937NicotinateHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 86742329N-succinimidyl-nicotinate2×HCID 86742330ethylamine DMF

Produkt 1

HCID 72663N-(2-hydroxyethyl)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The N-succinimidyl-nicotinate compound described in Example 1 was reacted with the hydrochloric salt of ethanolamine, available commercially in its radioactive form. The ethanolamine salt was dissolved in dried DMF and chilled in an ice bath. To the mixture was added an equimolar of diisopropylethylamine (DIEA) and stirred for 15 minutes. An equimolar solution of N-succinimidyl-nicotinate was added to the ethylamine-DMF mixture dropwise under a nitrogen atmosphere. As the nicotinate was added the mixture turned milky and was slurried for at least another half hour. The milky substance was the N-hydroxy-succinimide precipitating, which was filtered off. The DMF-mixture was washed with ether to remove any precipitant. The solvent mixture was removed under high vaccum. The oily mixture was triturated with ether to yield a precipitant, N-(2-hydroxyethyl)nicotinamide. The radioactive compound was isolated and identified by its TLC.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. customleast another half hour
  3. filtrationwas filtered off
  4. washThe DMF-mixture was washed with ether
  5. customto remove any precipitant
  6. customThe solvent mixture was removed under high vaccum
  7. customThe oily mixture was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-b5b09e4205d74d908c6d4d8044e0f888
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764462

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