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

HRID 54561

반응식

HRID 54561 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-50dec5ff3d014dcb9434de57ce76d919
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622976

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