Potassium Iodide → 2-[3-[4-[3-(Trifluoromethyl)phenyl]-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one

HRID 126780

反応式

HRID 126780 の反応式
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH2:7][CH2:6]1.[Na].[N:22]1[NH:23][C:24](=[O:31])[N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12.[I-].[K+]>[OH-].[K+].C(#N)C>[F:18][C:17]([F:20])([F:19])[C:13]1[CH:12]=[C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][N:23]3[C:24](=[O:31])[N:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]4=[N:22]3)[CH2:6][CH2:7]2)[CH:16]=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 814311,2,4-Triazolo(4,3-a)pyridin-3(2H)-oneHCID 3060362Piperazine, 1-(3-chloropropyl)-4-(3-(trifluoromethyl)phenyl)-2 回HCID 5360545Sodium

生成物 1

HCID 202879862-[3-[4-[3-(Trifluoromethyl)phenyl]-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 14797Potassium Hydroxide溶媒

実験手順

The hydrochloride salt of 1-(3-chloropropyl)-4-[3-(trifluoromethyl)phenyl]piperazine, 6.41 g. (0.0187 mole) is dissolved in dilute KOH solution and the free base which is formed is extracted into ether. The ether solution is washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford the desired free base. A suspension of 2.61 g. (0.0166 mole) of the sodium salt of 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one and 5.09 g (0.0166 mole) of 1-(3-chloropropyl)-4-[3-(trifluoromethyl)phenyl]piperazine in 100 ml. of acetonitrile is treated with approximately 50 mg. of potassium iodide, and refluxed for 24 hrs. The mixture is then cooled and filtered, and the filtrate concentrated to an oil under reduced pressure. The residual oil solidifies when triturated with ether. This solid is recrystallized twice from ethanol to give 4.34 g. (58%) of product, m.p. 207.5°-209.5°.

後処理

  1. customthe free base which is formed
  2. extractionis extracted into ether
  3. washThe ether solution is washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the desired free base
  7. additionA suspension of 2.61 g
  8. temperatureThe mixture is then cooled
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated to an oil under reduced pressure
  11. customtriturated with ether
  12. customThis solid is recrystallized twice from ethanol
  13. customto give 4.34 g

出典と根拠

ORDレコード
ord-0393b0cf2b554452a7bc58ad18c28ff1
出典データセット
uspto-grants-1981_03
特許番号
US04254124

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