Sodium Hydroxide → 3-[1-Hydroxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole

HRID 54567Notes

Reaction equation

C([O:4][CH:5]([C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[O:24][N:23]=1)[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)(=O)C.[OH-].[Na+]>CO>[OH:4][CH:5]([C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[O:24][N:23]=1)[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[1-acetoxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole (0.5 g) in methanol (10 ml) was added 4N an aqueous sodium hydroxide solution (0.5 ml) at 0° C. After stirring at 0° C. for 2 hours, ice water was added to the mixture and the precipitates were filtrated to give 3-[1-hydroxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole (0.44 g). The compound (100 mg) was dissolved in a solution of fumaric acid (27 mg) in ethanol to give 3-[1-hydroxy-4-(1-benzylpiperidin-4-yl)butyl]-5-(4-nitrophenyl)-1,2,4-oxadiazole fumarate (0.1 g).

Workup

filtrationthe precipitates were filtrated

Sources & evidence

ORD record: ord-14143b67ef8b41d599245890c23cb4d7
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622976

Reaction notes

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