Sodium hydride → HCID 19959229、化合物

HRID 54560ノート

反応式

HRID 54560 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 19959229HCID 19959229、化合物収率 26.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-48e48bb72ee04b2f81a39faadc7903ce
出典データセット
uspto-grants-1997_04
特許番号
US05622976

反応ノート

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