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Potassium Carbonate → 1-(1-Cyclopropylpiperazin-4-yl)-3-(4-methoxyphenyl)isoquinoline dihydrochloride

HRID 1006919
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HRID 1006919 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[ClH:20].[CH:21]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[ClH:1].[ClH:20].[CH:21]1([N:24]2[CH2:29][CH2:28][N:27]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[C:4]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[N:3]=3)[CH2:26][CH2:25]2)[CH2:23][CH2:22]1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinolineHCID 225027521-Cyclopropylpiperazine hydrochloride

생성물 1

HCID 226712261-(1-Cyclopropylpiperazin-4-yl)-3-(4-methoxyphenyl)isoquinoline dihydrochloride수율 16.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

1-Chloro-3-(4-methoxyphenyl)isoquinoline (514 mg), and 1-cyclopropylpiperazine hydrochloride salt (378 mg) described in JP-A 62-129273 were dissolved in dimethyl sulfoxide (7 ml) followed by the addition of potassium carbonate (788 mg), and the resulting mixture was stirred at 100° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system). The resulting product was converted into a hydrochloride in a conventional manner, and then recrystallized from ethanol/isopropyl ether, to give the hydrochloride of the title compound as yellow crystals (136 mg, yield; 16%).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe resulting organic layer was washed with water
  3. dry with materialdried (over MgSO4)
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)
  6. customrecrystallized from ethanol/isopropyl ether

출처 및 근거

ORD 기록
ord-4873826616704035b1d69b190d5e438a
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06790844B2

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