Sodium Iodide → 6-Iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

HRID 2112820ノート

反応式

HRID 2112820 の反応式
[Na+].[I-:2].CNCCNC.Br[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([N:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)[CH:14]=[C:13]2[CH3:27].CCOC(C)=O>O1CCOCC1.[Cu]I>[I:2][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([N:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)[CH:14]=[C:13]2[CH3:27]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 8857Ethyl AcetateHCID 690634506-Bromo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

生成物 1

HCID 690607816-Iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Under an argon atmosphere, 39 mg (0.2 mmol) of CuI, 0.6 g (4.0 mmol) of NaI, and 43 μL N,N′-dimethylethylenediamine are added to a solution of 0.69 g (2.0 mmol) of 6-bromo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline in 2 mL of 1,4-dioxane and the reaction mixture is shaken for 14 hours at 110° C. After cooling, it is combined with 60 mL of EtOAc, and the organic phase is washed twice with 20 mL of 5% NH3 solution and dried over magnesium sulfate. After the desiccant and solvent have been eliminated, the residue is reacted further without purification. Yield: 0.65 g (88% of theoretical); C16H19IN2 (M=366.240); calc.: molpeak (M+H)+: 367; found: molpeak (M+H)+: 367; HPLC-MS: 7.0 min (method A).

後処理

  1. temperatureAfter cooling
  2. washthe organic phase is washed twice with 20 mL of 5% NH3 solution
  3. dry with materialdried over magnesium sulfate
  4. customthe residue is reacted further without purification
  5. custom7.0 min (method A)

出典と根拠

ORDレコード
ord-413cbaef4ca045f0a9f6fb3e183d45ef
出典データセット
uspto-grants-2009_04
特許番号
US07524862B2

反応ノート

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