Benzylamine → 1-benzyl-5-(benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one

HRID 4111

Reaktionsgleichung

Reaktionsgleichung von HRID 4111
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[OH:1][CH2:2][C:3]1[N:25]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7](=[O:9])[CH:8]=1

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Produkt 1

HCID 41919451-benzyl-5-(benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-(hydroxymethyl)-5-(phenylmethoxy)-4H-pyran-4-one (10.5 g, 45.3 mmol) in benzylamine (40 ml) and water (60 ml) was refluxed for four hours and then stirred overnight at room temperature. The resulting precipitate was collected and washed thoroughly with water to give 9.17 g (28.6 mmol) of 2-(hydroxymethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)pyridinone (melting point 146°-147° C.) upon drying. The supernatant was diluted with water to a total volume of 450 ml, and after standing for one hour at room temperature, the resulting precipitate was collected to yield 2.47 g (7.69 mmol) of additional 2-(hydroxymethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone upon drying.

Aufarbeitung

  1. customThe resulting precipitate was collected
  2. washwashed thoroughly with water

Quellen und Nachweise

ORD-Eintrag
ord-5ddfe65b2c3c413f8c72b9a144125d66
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723002

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