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Triethylamine → 1-(4-Cyanobenzenesulphonyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl]piperazine

HRID 2289522
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HRID 2289522 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[N:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)=[N:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:30]2[CH2:29][CH2:28][N:27]([C:25]([CH:22]3[CH2:23][CH2:24][N:19]([C:16]4[CH:17]=[CH:18][N:13]=[CH:14][N:15]=4)[CH2:20][CH2:21]3)=[O:26])[CH2:32][CH2:31]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 186979701-[1-(4-Pyrimidinyl)-4-piperidylcarbonyl]piperazine

생성물 1

HCID 186980611-(4-Cyanobenzenesulphonyl)-4-[1-(4-pyrimidinyl)piperidin-4-ylcarbonyl]piperazine수율 42.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-cyanophenylsulphonyl chloride (363 mg) in dichloromethane (10 ml) was added to a stirred mixture of 1-[1-(4-pyrimidinyl)-4-piperidylcarbonyl] piperazine (412.5 mg) and triethylamine (0.28 ml) in dichloromethane (15 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between dichloromethane and water, and the organic phase washed with water, dried (Na2SO4) and evaporated. The residue was purified by column chromatography using 0.5% methanol in dichloromethane. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(4-cyanophenylsulphonyl)-4-[1-(4-pyrimidinyl)-4-piperidylcarbonyl] piperazine (280 mg), mp 180-181° C.;

후처리

  1. customThe mixture was partitioned between dichloromethane and water
  2. washthe organic phase washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. customRecrystallisation from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-a540351563c94ff09946ce42eb03d349
출처 데이터셋
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06093718

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