1-Methylpiperazine → HCID 57564982, compound

HRID 1726858Notes

Reaction equation

HRID 1726858 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.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CC(O)(CC)C.[Cl-].[Zn+2].[Cl-]>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[NH:9][C:10]([C:15]4[CH:20]=[C:19]([N:26]5[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]5)[CH:18]=[CH:17][N:16]=4)=[CH:11][C:12](=[O:14])[CH:13]=3)[CH:3]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 58781425HCID 58781425, compound

Product 1

HCID 57564982HCID 57564982, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 10.89 g (34.2 mmol) of 4,4″-dichloro-1′H-[2,2′;6′,2″]terpyridin-4′-one, 68.6 g (685 mmol, 76.1 ml) of 1-methylpiperazine and 233 mg (1.71 mmol, 0.05 equivalent) of zinc(II) chloride in 200 ml of 2-methyl-2-butanol is boiled under reflux for 24 hours. The mixture is evaporated to dryness on a rotary evaporator. The crude product is recrystallized from ethyl acetate/methanol 33:1 (v/v). It is taken up in 100 ml of water, adjusted to pH=8-9 with 4N sodium hydroxide solution, and light-beige 4,4″-bis(4methylpiperazin-1-yl)-1′H-[2,2′;6′,2″]terpyridin-4′-one is filtered off. 1H-NMR (360 MHz, CDCl3): 8.32 (d, 2H, J=5.9 Hz); 7.18 (dm, 2H); 6.93 (s, 2H); 6.66 (dd, 2H; J=5.9,2.3 Hz); 3.41-3.32 (tm, 8H); 2.55-2.44 (tm, 8H); 2.29 (s, 6H).

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe mixture is evaporated to dryness on a rotary evaporator
  3. customThe crude product is recrystallized from ethyl acetate/methanol 33:1 (v/v)
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-9e5515d1b4b146fba9c1423893b02e28
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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