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Pyridine → 6-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril

HRID 358500
ノート
印刷プレビュー

反応式

HRID 358500 の反応式
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([OH:3])=O.N1C=CC=CC=1.S(Cl)(Cl)=O.[CH2:25]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[CH2:25]([N:32]1[CH2:37][CH2:36][N:35]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3)=[O:3])[CH2:34][CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1049PyridineHCID 24386Thionyl Chloride2 回HCID 759941-BenzylpiperazineHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

生成物 1

HCID 131953356-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril

試薬・触媒・溶媒 3

HCID 887Methanol
溶媒
HCID 6212Chloroform溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

1.9 Grams of 6-carboxy-3,4-dihydrocarbostyril was suspended in 200 ml of methylene chloride, then 2 ml of pyridine was added to the suspension and under stirring 1.4 g of thionyl chloride was added dropwise in keeping the inside temperature at 0°-20° C. After the addition of thionyl chloride, the reaction mixture was kept at the same temperature and stirred for 1 hour, then 1.74 g of benzylpiperazine in 10 ml of methylene chloride solution was added to the mixture. Then the reaction mixture was further stirred at a room temperature for 4 hours. The reaction mixture was washed thoroughly with an aqueous solution of potassium carbonate, then washed with water and a diluted hydrochloric acid, dried with anhydrous sodium sulfate and the solvent was removed by distillation. The residue thus obtained was treated by a silica gel column chromatography (Silica gel: Wako C-200, eluate:chloroform:methanol (volume/volume)=20:1). The objective product was recrystallized from ethanol to obtain 325 mg of 6-(4-benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 198°-200° C.

後処理

  1. additionwas added dropwise
  2. customat 0°-20° C
  3. stirringThen the reaction mixture was further stirred at a room temperature for 4 hours
  4. washThe reaction mixture was washed thoroughly with an aqueous solution of potassium carbonate
  5. washwashed with water
  6. dry with materiala diluted hydrochloric acid, dried with anhydrous sodium sulfate
  7. customthe solvent was removed by distillation
  8. customThe residue thus obtained
  9. customThe objective product was recrystallized from ethanol

出典と根拠

ORDレコード
ord-340e3a5c8ddb49469ca5db38d17cb8fe
出典データセット
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04468402

反応ノート

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