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

HRID 479453ノート

反応式

HRID 479453 の反応式
[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

参加物

6

反応物 3

HCID 31268Pyrrolidine2 回HCID 740491-Methyl-4-piperidoneHCID 27373264'-Fluoro-2'-hydroxyacetophenone

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cf7252fc7327422b847871bbd1eef5ee
出典データセット
uspto-grants-2003_11
特許番号
US06645973B1

反応ノート

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