Chloroacetonitrile → 6-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazole

HRID 264272

反応式

HRID 264272 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+].Cl[CH2:24][C:25]#[N:26]>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][C:25]#[N:26])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

生成物 1

HCID 130783426-Fluoro-3-(1-cyanomethyl-4-piperidyl)-1,2-benzisoxazole

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, 61.6 mmol) and 2-chloroacetonitrile (5.5 g, 73 mmol) in acetonitrile (250 ml) was heated at reflux for 24 hours. The insolubles were filtered off and rinsed with methylene chloride (DCM). During concentration of the solvents on the rotary evaporator, crystals appeared. The crystals were collected and weighed 5.79 g. The product in the mother liquor was further purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, and 1%CH3OH in DCM). The second crop of product thus obtained weighed 5.2 g. The total yield was 10.9 g. The sample was recrystallized once more form ethanol, m.p. 130°-132° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe insolubles were filtered off
  4. washrinsed with methylene chloride (DCM)
  5. customDuring concentration of the solvents on the rotary evaporator, crystals
  6. customThe crystals were collected
  7. customThe product in the mother liquor was further purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, and 1%CH3OH in DCM)
  8. customThe second crop of product thus obtained
  9. customThe sample was recrystallized once more
  10. customform ethanol, m.p. 130°-132° C.

出典と根拠

ORDレコード
ord-3b3b90aba2b64a02afda0bb2367e2598
出典データセット
uspto-grants-1997_07
特許番号
US05646161

関連ノート

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