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Triethylamine → 1-(4-Ethylpiperidin-1-yl)-3-(4-methoxyphenyl)isoquinolinehydrochloride

HRID 1006955
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HRID 1006955 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.[CH2:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:21].C(N(CC)CC)C>CN(C)C=O>[ClH:1].[CH2:20]([CH:22]1[CH2:27][CH2:26][N:25]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:3]=2)[CH2:24][CH2:23]1)[CH3:21]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 767044-EthylpiperidineHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

생성물 1

HCID 225025221-(4-Ethylpiperidin-1-yl)-3-(4-methoxyphenyl)isoquinolinehydrochloride수율 15.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

1-Chloro-3-(4-methoxyphenyl)isoquinoline (405 mg) and 4-ethylpiperidine (168 mg) were dissolved in N,N-dimethylformamide (5 ml), followed by the addition of triethylamine (251 ml), and the mixture was stirred at 80° 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 (ethyl acetate/hexane system). Then 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 a colorless crystals (87 mg, yield; 13%).

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 (ethyl acetate/hexane system)
  6. customrecrystallized from ethanol/isopropyl ether

출처 및 근거

ORD 기록
ord-c2af1ab155824703bebf4cabb2f0d6e2
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06790844B2

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