Benzaldehyde → N-[2-(benzylamino)ethyl]pyridine-3-carboxamide

HRID 1589201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589201
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 240BenzaldehydeHCID 571799SG 1842

Produkt 1

HCID 4242394N-[2-(benzylamino)ethyl]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(2-aminoethyl)pyridine-3-carboxamide (26.5 g.) and benzaldehyde (16.35 ml.) in ethanol (220 ml.) was kept for 48 hours. A small quantity of solid was removed by filtration. Sodium borohydride (6.1 g.) was then added to the filtrate which was stirred for 1 hour. Glacial acetic acid was then added cautiously until the solution was neutral. The solution was diluted with water (100 ml.) and basified with 2M sodium hydroxide. The mixture was extracted with ethyl acetate (3×200 ml.) and the extracts washed with saturated brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a column of Florisil (200 g.), eluting with ethyl acetate, to yield N-[2-(benzylamino)ethyl]pyridine-3-carboxamide (29.5 g.) as a pale brown oil.

Aufarbeitung

  1. customA small quantity of solid was removed by filtration
  2. additionSodium borohydride (6.1 g.) was then added to the filtrate which
  3. additionGlacial acetic acid was then added cautiously until the solution
  4. additionThe solution was diluted with water (100 ml.)
  5. extractionThe mixture was extracted with ethyl acetate (3×200 ml.)
  6. washthe extracts washed with saturated brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by chromatography on a column of Florisil (200 g.)
  10. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7a9c8347d88d4f9090754c71dd962048
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04568691

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