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Water → 3-[3-(1-Benzylpiperidin-4-yl)propyl]-5-(quinuclidin-3-yl)-1,2,4-oxadiazole

HRID 54561
Notes
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Reaction equation

HRID 54561 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17](=[N:19][OH:20])[NH2:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[N:23]12[CH2:30][CH2:29][CH:26]([CH2:27][CH2:28]1)[CH:25]([C:31](OC)=O)[CH2:24]2.O>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][C:17]2[N:18]=[C:31]([CH:25]3[CH:26]4[CH2:29][CH2:30][N:23]([CH2:28][CH2:27]4)[CH2:24]3)[O:20][N:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2736953Methyl quinuclidine-3-carboxylateHCID 867507264-(1-Benzylpiperidin-4-yl)butanamide oxime

Product 1

HCID 199591603-[3-(1-Benzylpiperidin-4-yl)propyl]-5-(quinuclidin-3-yl)-1,2,4-oxadiazoleYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A mixture of 4-(1-benzylpiperidin-4-yl)butanamide oxime (1.0 g), sodium hydride (0.15 g) and molecular sieves 4A (2.0 g) in tetrahydrofuran (50 ml) was stirred at ambient temperature for 30 minutes. To the mixture was added dropwise a solution of methyl 3-quinuclidine carboxylate (0.49 g) in tetrahydrofuran (10 ml) and refluxed for 6 hours. After cooling to room temperature, the mixture was poured into water and extracted with ethyl acetate. The extracts were successively washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on alumina eluting with chloroform to give 3-[3-(1-benzylpiperidin-4-yl)propyl]-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.5 g) as an oil.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extracts were successively washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on alumina eluting with chloroform

Sources & evidence

ORD record
ord-50dec5ff3d014dcb9434de57ce76d919
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05622976

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes