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

HRID 54568Notes

Reaction equation

HRID 54568 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2ba95f3b1b414783bfb09c02813a34a8
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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