2-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine → 3-[1-Acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole

HRID 54565Notes

Reaction equation

HRID 54565 reaction equation
[C:1]([O:4][CH:5]([CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1)[C:6]([NH2:20])=[N:7][O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=[O:3])[CH3:2]>O1CCOCC1>[C:1]([O:4][CH:5]([C:6]1[N:20]=[C:9]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[O:8][N:7]=1)[CH2:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 540644882-Acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine

Product 1

HCID 199591703-[1-Acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazoleYield 43.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of 2-acetoxy-5-(1-benzylpiperidin-4-yl)-1-(4-nitrobenzoyloxyimino)pentylamine (1.5 g) and molecular sieves 4A (7.5 g) in dioxane (50 ml) was refluxed for 2 hours. After molecular sieves were removed by filtration, the filtrate was evaporated in vacuo. The residue was chromatographed on silica eluting with 3% methanol in chloroform to give 3-[1-acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole (0.63 g, 43.6%). The compound (74 mg) was dissolved in a solution of fumaric acid (18 mg) in ethanol to give 3-[1-acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole fumarate (80 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter molecular sieves were removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was chromatographed on silica eluting with 3% methanol in chloroform

Sources & evidence

ORD record
ord-660f3d0b148a4ed786a35eb7d7bd2fc9
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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