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

HRID 1643432

반응식

HRID 1643432 반응식
[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

참가 물질

11

반응물 5

HCID 63612-ChloropropaneHCID 112011,1-DibromoethaneHCID 122863-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 5462224Magnesium2회

생성물 1

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

시약·촉매·용매 5

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

(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%)

후처리

  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

출처 및 근거

ORD 기록
ord-8bda3eca92724b44aa900d46182fdf71
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119805B2

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