1-(2-Hydroxyethyl)piperazine → 2,6-Bis(2-pyridyl)-4(1H)-pyridone

HRID 1726861Notes

Reaction equation

HRID 1726861 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:9][C:10]([C:15]3[CH:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=3)=[CH:11][C:12](=[O:14])[CH:13]=2)[CH:3]=1.OCCN1CCNCC1>ClC1C=CC=CC=1>[N:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:8]1[NH:9][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:11][C:12](=[O:14])[CH:13]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 58781425HCID 58781425, compound

Product 1

HCID 6193532,6-Bis(2-pyridyl)-4(1H)-pyridone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 3.18 9 (10 mmol) 4,4″-dichlor-1′H-[2,2′;6′,2″]terpyridin-4′-on, 5.21 g (40 mmol) 1-(2-hydroxyethyl)-piperazin, and 30 mg Zn(II)-chloride in 300 ml chlorobenzol is refluxed for 18 hours. Afterwards the solution is concentrated by a rotary evaporator. The raw product is recrystallized from 40 ml water respectively 30 ml methanol. The whitish 4,4″-Bis-[4-(2-hydroxy-ethyl)-piperazin-1-yl)]-1′H-[2,2′;6′,2″]terpyridin-4′-on is obtained.

Workup

  1. temperatureis refluxed for 18 hours
  2. concentrationAfterwards the solution is concentrated by a rotary evaporator
  3. customThe raw product is recrystallized from 40 ml water respectively 30 ml methanol

Sources & evidence

ORD record
ord-f3a5d9a275ec43218600b47af3821ea1
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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