Sodium hydride → HCID 19959229, compound

HRID 54560Notes

Reaction equation

HRID 54560 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]=[C:7]([CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[O:6][N:5]=1.Cl.[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32](Cl)=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([NH:3][C:4]2[N:8]=[C:7]([CH:9]3[CH:14]4[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]4)[CH2:10]3)[O:6][N:5]=2)=[O:33])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1951113-(3-Amino-1,2,4-oxadiazole-5-yl)-quinuclidineHCID 19959133(1-Benzylpiperidin-4-yl)acetyl chloride hydrochloride

Product 1

HCID 19959229HCID 19959229, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.4 g) in N,N-dimethylformamide was added 3-amino-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.2 g) at 0° C. and the mixture was stirred for 1 hour. To the mixture was added (1-benzylpiperidin-4-yl)acetyl chloride hydrochloride (2.53 g) during 30 minutes at 0° C. After stirred for additional 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The extract was washed with water, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on alumina with chloroform to give 3-{(1-benzylpiperidin-4-yl)acetylamino}-5-(quinuclidin-3-yl)-1,2,4-oxadiazole (0.11 g).

Workup

  1. stirringAfter stirred for additional 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on alumina with chloroform

Sources & evidence

ORD record
ord-48e48bb72ee04b2f81a39faadc7903ce
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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