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Triethylamine → 4-Amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinoline hydrochloride hydrate

HRID 542205
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HRID 542205 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[C:11]([Cl:13])=[O:12].[NH2:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[C:17]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH2:1].[ClH:13].[NH2:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[C:17]([N:29]2[CH2:30][CH2:31][N:32]([C:11]([CH:2]3[O:1][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3]3)=[O:12])[CH2:33][CH2:34]2)[CH:16]=1
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반응물 3

HCID 8471TriethylamineHCID 27354472,3-Dihydro-1,4-benzodioxin-2-carbonyl chlorideHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

생성물 1

HCID 201311304-Amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinoline hydrochloride hydrate수율 29.4%

시약·촉매·용매 1

HCID 6212Chloroform
용매
2회

실험 절차

A solution of 1,4-benzodioxan-2-carbonyl chloride (0.75 g) in chloroform (10 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.0 g) in chloroform (50 ml) with triethylamine (1.06 g) at 5°-10°. The reaction was stirred at 5°-10° for one hour, then allowed to attain room temperature and stirred overnight. The mixture was then evaporated in vacuo and the residue partitioned between chloroform (50 ml) and sodium carbonate solution (10%, 50 ml). The chloroform layer was separated, the aqueous phase extracted with chloroform (2×50 ml), the extracts combined, washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was then taken up in chloroform and chromatographed on silica (Merck 9385, 60 g) eluting with chloroform/methanol (100:0→97:3). A solution of the purified product in chloroform was treated with ethereal hydrogen chloride, evaporated in vacuo and the residue recrystallised from isopropanol to give 4-amino-2-[ 4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinoline hydrochloride hydrate (0.28 g), m.p. 201°.

후처리

  1. customto attain room temperature
  2. stirringstirred overnight
  3. customThe mixture was then evaporated in vacuo
  4. customthe residue partitioned between chloroform (50 ml) and sodium carbonate solution (10%, 50 ml)
  5. customThe chloroform layer was separated
  6. extractionthe aqueous phase extracted with chloroform (2×50 ml)
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customchromatographed on silica (Merck 9385, 60 g)
  11. washeluting with chloroform/methanol (100:0→97:3)
  12. additionA solution of the purified product in chloroform was treated with ethereal hydrogen chloride
  13. customevaporated in vacuo
  14. customthe residue recrystallised from isopropanol

출처 및 근거

ORD 기록
ord-92c931bc07db44f19c3486c407731037
출처 데이터셋
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04656174

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