2-(4-Fluorophenyl)oxirane → 1-[2-Hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

HRID 497353

반응식

HRID 497353 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(O)C>[OH:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:10][N:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][CH2:23][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][C:13]=2[O:12][CH3:11])[CH2:32][CH2:31]1

참가 물질

4

반응물 2

HCID 40652302-(4-Fluorophenyl)oxiraneHCID 223186531-[4-(2-Methoxynaphthalen-1-yl)butyl]piperazine

생성물 1

HCID 223186441-[2-Hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

0.80 g of the optically active form of 2-(4-fluorophenyl)oxirane was dissolved in ethanol, and 3.2 g of 1-[4-(2-methoxynaphthalen-1-yl)butyl]piperazine was added, followed by reflux with heating or 2 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in chloroform and washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1) to give 1.2 g of optically active 1-[2-hydroxy-2-(4-fluorophenyl)ethyl]-4-[4-(2-methoxynaphthalen-1-yl)butyl]piperazin as a solid.

후처리

  1. temperatureby reflux
  2. temperaturewith heating or 2 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-e965505911144bbd8466f4ae43d923ea
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949552B2

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