Nitrogen mustard hydrochloride → 3-Bromo-8-(4-methyl-piperazin-1-yl)-quinoline

HRID 271129

반응식

HRID 271129 반응식
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].C(=O)([O-])[O-].[Na+].[Na+].[Br:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:27]>C(O)CCC.ClCCl>[Br:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[N:27]1[CH2:8][CH2:7][N:5]([CH3:6])[CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 151125453-Bromoquinolin-8-amine

생성물 1

HCID 673136243-Bromo-8-(4-methyl-piperazin-1-yl)-quinoline수율 49%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 6344Dichloromethane용매

실험 절차

bis-(2-Chloro-ethyl)-methyl-amine hydrochloride (3.7 g, 19.2 mmol) and sodium carbonate (9.0 g, 85 mmol) were added to a suspension of 3-bromo-quinolin-8-ylamine (3.9 g, 17.5 mmol) (for synthesis see Gershon et al., Monatsh. Chem., 1991, 122, 935) in n-butanol (70 ml). The stirred suspension was heated at reflux for 72 h. The reaction mixture was cooled to ambient temperature, diluted with dichloromethane (300 ml) and the solution washed with water (300 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane to afford the title compound (D1) as an oil (2.6 g, 8.5 mmol, 49%);

후처리

  1. temperatureThe stirred suspension was heated
  2. temperatureat reflux for 72 h
  3. washthe solution washed with water (300 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to an oil
  6. customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane

출처 및 근거

ORD 기록
ord-4a128299e4d74e9bad1f5963b56a11e9
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452888B2

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