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1-(2-Methoxyphenyl)piperazine → 2,3-dimethoxy-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}benzamide

HRID 638160
ノート
印刷プレビュー

反応式

HRID 638160 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Br.[NH2:16][CH2:17][CH2:18]Br.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(OCC)(=O)C.C(O)CCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:18][CH2:17][NH:16][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:29]=2[O:28][CH3:27])[CH2:11][CH2:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 27583922,3-Dimethoxybenzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

生成物 1

HCID 133184852,3-dimethoxy-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}benzamide収率 50%

試薬・触媒・溶媒 2

HCID 263
1-Butanol
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To 1.92 g (0.01 mol) of 1-(2-methoxyphenyl)piperazine, 2,05 g (0.01 mol) of 2-aminoethylbromide hydrobromide, 2.5 g of triethylamine and 20 ml of n-butanol were added, and the mixture was refluxed for 6 hours. After the reaction, the mixture was concentrated under vacuum, and to the resulting residue, 2.5 g of anhydrous sodium carbonate, 20 ml of water and 20 ml of ethyl acetate were added. Under agitation with cooling on ice, a solution of 2.2 g (0.011 mol) of 2,3-dimethoxybenzoyl chloride in a small amount of ethyl acetate was added dropwise to the mixture. Thereafter, the mixture was stirred for 30 minutes under cooling with ice and extracted with ethyl acetate by agitation for 30 minutes at room temperature. The separated organic layer was washed with water, and 1N HCl was added until the pH became 3.0. The aqueous layer was separated, neutralized with sodium hydroxide and extracted with ethyl acetate. The resulting organic layer was washed with water, dried with Glauber's salt and concentrated under vacuum. The residue was subjected to column chromatography on silica gel (solvent: chloroform/methanol=100:1) to provide 1.99 g (yield: 50%) of 1-(2-methoxyphenyl)-4[2-(2,3-dimethoxybenzoyl)aminoethyl]piperazine. Recrystallization from isopropanol gave a colorless acicular crystal having a melting point of 133°-134° C.

後処理

  1. temperaturethe mixture was refluxed for 6 hours
  2. customAfter the reaction
  3. concentrationthe mixture was concentrated under vacuum
  4. additionto the resulting residue, 2.5 g of anhydrous sodium carbonate, 20 ml of water and 20 ml of ethyl acetate were added
  5. temperatureUnder agitation with cooling on ice
  6. temperatureunder cooling with ice
  7. extractionextracted with ethyl acetate by agitation for 30 minutes at room temperature
  8. washThe separated organic layer was washed with water, and 1N HCl
  9. additionwas added until the pH
  10. customThe aqueous layer was separated
  11. extractionextracted with ethyl acetate
  12. washThe resulting organic layer was washed with water
  13. dry with materialdried with Glauber's salt
  14. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-9d63571007234cb9b1f2c224c304f6d2
出典データセット
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04560686

反応ノート

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