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

HRID 883519

反応式

HRID 883519 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%);

後処理

  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

出典と根拠

ORDレコード
ord-f8057e4ece724fa39968601bee0eb2f3
出典データセット
uspto-grants-2012_08
特許番号
US08236947B2

関連ノート

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