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

HRID 4111

Reaction equation

HRID 4111 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5ddfe65b2c3c413f8c72b9a144125d66
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Linked notes

Loading…