Ammonium Chloride → 3-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

HRID 15772

反応式

HRID 15772 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)[CH2:14][CH2:13]2)[N:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[NH2:26])[CH2:16][CH2:17]2)[N:3]=1

参加物

6

反応物 2

HCID 25517Ammonium Chloride2 回HCID 498519022-Methyl-5-(4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

生成物 1

HCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline収率 84%

試薬・触媒・溶媒 3

HCID 23925Iron触媒2 回HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline (D5) (0.14 g; 1 eq) in methanol (3 mL) was added dropwise to a suspension of iron powder (0.07 g; 3.2 eq) and ammonium chloride (0.1 g; 5.3 eq) in water (3 mL). The reactants were heated at reflux for 8 hours, adding additional amounts of iron powder (total 0.07 g; 3.2 eq) and ammonium chloride (total 0.1 g; 5.03 eq) in 3 portions during the reaction. The reaction mixture was filtered using a Millipore filter. The filtrate was concentrated under reduced pressure, diluted with water (5 mL) and a saturated aqueous solution of sodium hydrogen carbonate (2 mL), extracted into ethyl acetate (3×5 mL), dried over Na2SO4 and concentrated under reduced pressure obtaining the title compound in 84% yield (0.11 g).

後処理

  1. temperatureThe reactants were heated
  2. temperatureat reflux for 8 hours
  3. customduring the reaction
  4. filtrationThe reaction mixture was filtered
  5. filtrationfilter
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additiondiluted with water (5 mL)
  8. extractiona saturated aqueous solution of sodium hydrogen carbonate (2 mL), extracted into ethyl acetate (3×5 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b07f56696d174612beb8a424b503ba80
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

読み込み中…