1-Methylpiperazine → 4-(4-Methyl-piperazin-1-yl)-1'H-[2,2';6',2'']terpyridin-4'-one

HRID 1726855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1726855
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:9][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:11][C:12](=[O:14])[CH:13]=2)[CH:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC(O)(CC)C.[Cl-].[Zn+2].[Cl-]>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[NH:9][C:10]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)=[CH:11][C:12](=[O:14])[CH:13]=3)[CH:3]=2)[CH2:24][CH2:23]1

Komponenten

5

Edukt 2

HCID 531671-MethylpiperazineHCID 575649954-chloro-1'H-[2,2';6',2'']terpyridin-4'-one

Produkt 1

HCID 575649904-(4-Methyl-piperazin-1-yl)-1'H-[2,2';6',2'']terpyridin-4'-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 64052-Methyl-2-butanolLösungsmittel

Versuchsvorschrift

A mixture of 5.22 g (18.4 mmol) of 4-chloro-1′H-[2,2′;6′,2″]terpyridin-4′-one, 18.36 g (184 mmol, 20.4 ml) of 1-methylpiperazine and 125 mg (0.92 mmol, 0.05 equivalent) of zinc(II) chloride in 80 ml of 2-methyl-2-butanol is boiled under reflux for 30 hours. The mixture is evaporated to dryness on a rotary evaporator. 100 ml of water are added and the mixture is rendered neutral with concentrated hydrochloric acid. Extracting the mixture four times with chloroform and combining and drying (sodium sulfate) the organic extracts gives the crude product which is subsequently recrystallized from acetonitrile. 4-(4-Methyl-piperazin-1-yl)-1′H-[2,2′;6′,2″]terpyridin-4′-one is obtained as a white solid. 1H-NMR (360 MHz, CDCl3): 8.69 (d, 1H, 4.5 Hz); 8.32 (d, 1H, J=5.9 Hz); 7.92-7.74 (m, 2H); 7.37-7.30 (m, 1H); 7.20 (d, 1H, J=2.3 Hz); 7.01 (s, 1H); 6.98 (s, 1H); 6.71-6.63 (m, 1H); 3.45-3.35(tm, 4H); 2.58-2.48 (tm, 4H); 2.32 (s, 3H).

Aufarbeitung

  1. temperatureunder reflux for 30 hours
  2. customThe mixture is evaporated to dryness on a rotary evaporator
  3. addition100 ml of water are added
  4. extractionExtracting the mixture four times with chloroform
  5. dry with materialdrying (sodium sulfate) the organic extracts
  6. customgives the crude product which
  7. customis subsequently recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-37f4a7d5a6924ec6b90f9f2ec8dd1fab
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07494964B2

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