Sodium Hydroxide → 1-(N-Methyl-2-piperidinyl)methyl-3-(3-quinolinecarbonyl)-1H-indole

HRID 1161610

반응식

HRID 1161610 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15](Cl)=[O:16])[CH:6]=1.[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1.[OH-].[Na+]>C(Cl)Cl>[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[CH2:25][N:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:15]([C:7]2[CH:6]=[N:5][C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:16])=[CH:27]1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 11030631Quinoline-3-carbonyl ChlorideHCID 11550392N-(N-Methylpiperidinyl)methylindole

생성물 1

HCID 101568091-(N-Methyl-2-piperidinyl)methyl-3-(3-quinolinecarbonyl)-1H-indole

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
23.5 °C

실험 절차

To the suspension of 200 mg (1.5 mmol) of anhydrous AlCl3 in 8 ml absolute methylene chloride was added 287.4 mg (1.5 mmol) 3-quinolinecarbonyl chloride in 5 ml methylene chloride and the reaction mixture was stirred 30 min at room 22-25° C. The (N-Methyl-2-piperidinyl)methyl-1H-indole 228.3 mg (1.0 mmol) in 5 ml of methylene chloride was added by dropwise during 1.5 h and the mixture stirred 36 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml). The combined extract dried by sodium sulfate. After removing of solvents the rest (0.365 g) was purified by chromatography (silica gel, toluene-triethylamine, 10:1).

후처리

  1. stirringthe mixture stirred 36 h
  2. extractionextracted by ethyl acetate (3×20 ml)
  3. extractionThe combined extract
  4. dry with materialdried by sodium sulfate
  5. customAfter removing of solvents the rest (0.365 g)
  6. customwas purified by chromatography (silica gel, toluene-triethylamine, 10:1)

출처 및 근거

ORD 기록
ord-6b08ba8816a84485a2ac41fdbcd3abd7
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820144B2

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