Potassium Carbonate → 3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionitrile

HRID 55708

反応式

HRID 55708 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][C:26]#[N:27]>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][C:26]#[N:27])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 170203-BromopropionitrileHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

生成物 1

HCID 184672443-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionitrile収率 31.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (11 g, 50 mmol), K2CO3 (8.5 g, 74 mmol) and 3-bromopropionitrile (8.2 g, 1.2 eq) in acetonitrile (300 ml) was heated at reflux for 24 hours. The mixture was cooled and the insolubles were filtered. The solvent was removed on a rotary evaporator and the crude product was purified by flash chromatography over a silica gel column (SiO2, 120 g). The product thus purified weighed 8.94 g. Recrystallization from ethanol yielded the nitrile as white crystals 4.3 g, m.p. 100°-101° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe insolubles were filtered
  5. customThe solvent was removed on a rotary evaporator
  6. customthe crude product was purified by flash chromatography over a silica gel column (SiO2, 120 g)
  7. customThe product thus purified
  8. customRecrystallization from ethanol

出典と根拠

ORDレコード
ord-857662e96a984888a8b6cb597c619328
出典データセット
uspto-grants-1997_04
特許番号
US05624927

関連ノート

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