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

HRID 15772

반응식

HRID 15772 반응식
[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

참가 물질

6

반응물 2

HCID 25517Ammonium Chloride2회HCID 498519022-Methyl-5-(4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매2회HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b07f56696d174612beb8a424b503ba80
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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