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Potassium Carbonate → (S)-N-(1-(2-(4-cyanophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992282
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HRID 992282 반응식
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)=[O:8])[CH2:2]1.C1(C)C=CC(S(O[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]34[CH2:18][CH:13]5[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]5)[CH2:10]3)[CH2:16]4)=[O:8])[CH2:2]2)=[CH:32][CH:33]=1)#[N:38]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 22033501HCID 22033501, 화합물HCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

생성물 1

HCID 9907753(S)-N-(1-(2-(4-cyanophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide수율 73.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

(S)-N-(Pyrrolidin-3-yl)-1-adamantanecarboxamide (1.0 g) and 2-(4-cyanophenyl)ethyl p-toluenesulfonate (1.2 g) were dissolved in acetonitrile, and potassium carbonate was added thereto. The mixture was stirred under heating at 70° C. for 5 hours. After the completion of the reaction, the solvent was evaporated under reduced pressure. Ethyl acetate was added to the obtained residue and the mixture was washed with saturated brine. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (chloroform:methanol=30:1). The obtained eluate was concentrated and IPE was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(1-(2-(4-cyanophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide (1.1 g), melting point 104-105° C.

후처리

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the obtained residue
  4. washthe mixture was washed with saturated brine
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe obtained eluate was concentrated
  7. additionIPE was added to the obtained residue
  8. filtrationThe precipitated crystals were collected by filtration

출처 및 근거

ORD 기록
ord-6aa3ed44ee8e49d99c01d0e9d9726089
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06468998B1

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