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

HRID 54568노트

반응식

HRID 54568 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2ba95f3b1b414783bfb09c02813a34a8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622976

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