Methane → Cetirizine amide

HRID 481988ノート

反応式

HRID 481988 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][C:26]([NH2:28])=[O:27].C(=O)([O-])[O-].[Na+].[Na+].C>[I-].[K+].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:22][CH2:23][O:24][CH2:25][C:26]([NH2:28])=[O:27])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 297MethaneHCID 9340NorchlorcyclizineHCID 10340Sodium CarbonateHCID 110189312-(2-Chloroethoxy)acetamide

生成物 1

HCID 3068840Cetirizine amide収率 79.6%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 1140Toluene溶媒

実験手順

77 g (0.2685 mole) of levorotatory (-)-1-[(4-chlorophenyl)phenylmethyl]piperazine (prepared in Example 4.1), 40.5 g (0.2932 mole) of 2-(2-chloroethoxy)acetamide, 62.8 g (0.591 mole) of sodium carbonate and 2 g (0.0120 mole) of potassium iodide are added to 700 ml of toluene. The mixture is heated at reflux temperature for 24 hours. 10 g of Norit are then added and the mixture is filtered while hot through Dicalite. The filtrate is washed with 500 ml of water and then with 500 ml of a saturated aqueous solution of sodium chloride. The organic phase is separated and dried over 250 g of sodium sulfate. It is then filtered and the solvent is evaporated. The residual oil is taken up in 1500 ml of hot diisopropyl oxide. The solution is heated under reflux and allowed to crystallize by cooling in an ice bath. The crystals are filtered, washed with a small amount of diisopropyl oxide and dried under vacuum at 40° C. 82.91 g of levorotatory (-)-2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetamide are obtained.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 24 hours
  3. filtrationthe mixture is filtered while hot through Dicalite
  4. washThe filtrate is washed with 500 ml of water
  5. customThe organic phase is separated
  6. dry with materialdried over 250 g of sodium sulfate
  7. filtrationIt is then filtered
  8. customthe solvent is evaporated
  9. temperatureThe solution is heated
  10. temperatureunder reflux
  11. customto crystallize
  12. temperatureby cooling in an ice bath
  13. filtrationThe crystals are filtered
  14. washwashed with a small amount of diisopropyl oxide
  15. customdried under vacuum at 40° C

出典と根拠

ORDレコード
ord-2a5e81e03d724d4a9aa9ae06e83a569d
出典データセット
uspto-grants-1998_08
特許番号
US05792770

反応ノート

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