2-Chloropropane → 1-Benzyl-4-(pyridin-3-YL)piperidin-4-OL

HRID 1643432ノート

反応式

HRID 1643432 の反応式
[Mg].BrC(Br)C.C(Cl)(C)C.Br[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.C(Cl)(Cl)Cl.O.CO.CCOCC>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)([OH:30])[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

11

反応物 5

HCID 63612-ChloropropaneHCID 112011,1-DibromoethaneHCID 122863-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 5462224Magnesium2 回

生成物 1

HCID 10940791-Benzyl-4-(pyridin-3-YL)piperidin-4-OL

試薬・触媒・溶媒 5

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(Apparatus: 1 I three-necked flask with nitrogen balloon) Magnesium (5.7 g) was initially introduced into anhydrous ether (125 ml), 1,1-dibromoethane (0.5 g) and isopropyl chloride (17.3 ml) were added dropwise and the mixture was stirred for 15 min to initiate the magnesium. A solution of 3-bromopyridine (25 g) in anhydrous tetrahydrofuran (400 ml) was added dropwise at 40° C. over the course of 20 min and the mixture was then refluxed for 2 h. A solution of 1-benzylpiperidin-4-one (30 g) in anhydrous tetrahydrofuran (100 ml) was finally added dropwise at 40° C. over the course of 20 min and the mixture was stirred at room temperature overnight. Thin layer chromatography control: 10% methanol in chloroform. The reaction mixture was hydrolysed with water (50 ml) at 0° C. and filtered over Celite. Extraction was carried out with methylene chloride (2×100 ml) and the combined organic phases were washed with water (50 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (Alox neutral) with 5% methanol in chloroform. Yield: 8.2 g (19%)

後処理

  1. additionwere added dropwise
  2. temperaturethe mixture was then refluxed for 2 h
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationfiltered over Celite
  5. extractionExtraction
  6. washthe combined organic phases were washed with water (50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (Alox neutral) with 5% methanol in chloroform

出典と根拠

ORDレコード
ord-8bda3eca92724b44aa900d46182fdf71
出典データセット
uspto-grants-2012_02
特許番号
US08119805B2

反応ノート

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