Potassium Carbonate → N-[2,3-Epoxypropyl)-4-(6fluoro-1,2-benzisoxazol-3-yl)piperidine fumarate

HRID 55669

反応式

HRID 55669 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:17]([O-:20])([O-:19])=O.[K+].[K+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Br>C(#N)C>[C:4]([OH:27])(=[O:8])/[CH:5]=[CH:15]/[C:17]([OH:20])=[O:19].[O:27]1[CH2:26][CH:25]1[CH2:23][N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

生成物 1

HCID 18467317N-[2,3-Epoxypropyl)-4-(6fluoro-1,2-benzisoxazol-3-yl)piperidine fumarate収率 33.3%

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 (7.5 g, 54 mmol) and epibromohydrin (9 g, 54 mmol) in acetonitrile (150 ml) was heated at reflux for 16 hours. The mixture was filtered and concentrated to dryness. The crude product was purified by flash chromatography (SiO2, 180 g, eluted with methylene chloride (DCM), and 1-2% CH3OH in DCM). The material thus purified as off-white solids weighed 8.7 g (63%). This material (3 g) was converted to fumarate salt in ethanol and isopropyl ether to give 3.27 g of white crystals, m.p.=145°-147° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash chromatography (SiO2, 180 g, eluted with methylene chloride (DCM), and 1-2% CH3OH in DCM)
  6. customThe material thus purified as off-white solids

出典と根拠

ORDレコード
ord-d4b10016c9044d4a80e08540268be8f4
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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