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

HRID 1726855ノート

反応式

HRID 1726855 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 64052-Methyl-2-butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-37f4a7d5a6924ec6b90f9f2ec8dd1fab
出典データセット
uspto-grants-2009_02
特許番号
US07494964B2

反応ノート

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