Phosphoric Acid → 3-[1-Oxo-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole

HRID 54568ノート

反応式

HRID 54568 の反応式
[OH:1][CH:2]([C:19]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[O:21][N:20]=1)[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.OP(O)(O)=O>CS(C)=O>[O:1]=[C:2]([C:19]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[O:21][N:20]=1)[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 1004Phosphoric AcidHCID 199592433-[1-Hydroxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole

生成物 1

HCID 199591993-[1-Oxo-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole収率 75.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

The mixture of 3-[1-hydroxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole (0.28 g), N,N-dicyclohexylcarbodiimide (0.66 g) and o-phosphoric acid (0.31 g) in dimethyl sulfoxide (5 ml) was stirred overnight at ambient temperature and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica eluting with 3% methanol in chloroform to give 3-[1-oxo-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole as an oil (0.21 g). The oil was dissolved in a solution of fumaric acid (48 mg) in ethanol and the crystals were filtered off to give 3-[1-oxo-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole fumarate (0.18 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica eluting with 3% methanol in chloroform

出典と根拠

ORDレコード
ord-2ba95f3b1b414783bfb09c02813a34a8
出典データセット
uspto-grants-1997_04
特許番号
US05622976

反応ノート

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