Pyrrolidine → 7-Fluoro-n-methylspiro[2h-1-benzopyran-2,4'-piperidine]-4(3h)one

HRID 479453

반응식

HRID 479453 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.N1CCCC1>CO.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8](=[O:10])[CH2:9][C:16]3([O:11][C:4]=2[CH:3]=1)[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]3

참가 물질

6

반응물 3

HCID 31268Pyrrolidine2회HCID 740491-Methyl-4-piperidoneHCID 27373264'-Fluoro-2'-hydroxyacetophenone

생성물 1

HCID 187709727-Fluoro-n-methylspiro[2h-1-benzopyran-2,4'-piperidine]-4(3h)one

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

A stirred solution of 4′-fluoro-2′-hydroxyacetophenone (15.97 g), 1-methyl-4-piperidone (12.74 cm3) and pyrrolidine (4.325 cm3) in methyl alcohol (250 cm3) was heated to reflux under nitrogen. After 0.5 h, further pyrrolidine (4.33 cm3) was added and, after another 0.5 h, the solution was allowed to cool. The reaction mixture was then evaporated under reduced pressure to give an oil, which was dissolved in dichloromethane (400 cm3). This solution was washed with water (3×400 cm3), dried (Na2SO4) and evaporated to give an oil (25.7 g). Flash chromatography on silica (eluting with dichloromethane-methyl alcohol-33% aqueous ammonia=380:20:1) gave the purified product as an oil (14.41 g).

후처리

  1. temperatureto reflux under nitrogen
  2. temperatureto cool
  3. customThe reaction mixture was then evaporated under reduced pressure
  4. customto give an oil, which
  5. washThis solution was washed with water (3×400 cm3)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-cf7252fc7327422b847871bbd1eef5ee
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645973B1

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