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Pyridine → 1-(3-Methoxy phenyl)-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide

HRID 26205
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반응식

HRID 26205 반응식
Cl[C:2]1[N:3]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:4]2[C:9]([C:10]=1[C:11](Cl)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.N1C=CC=CC=1.[NH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C:2]=2[N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[O:12])[CH2:25][CH2:24]1
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참가 물질

7

반응물 4

HCID 1049PyridineHCID 4837PiperazineHCID 531671-MethylpiperazineHCID 53923702HCID 53923702, 화합물

생성물 1

HCID 867364561-(3-Methoxy phenyl)-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide

시약·촉매·용매 2

HCID 6212Chloroform용매2회
HCID 6344Dichloromethane용매

실험 절차

To a solution of 3.2 g (10 mmols) of 2-chloro-1-(3-methoxyphenyl)-indole 3-carboxylic acid chloride in 20 ml of chloroform, a mixture pf 2.2 ml of N-methyl-piperazine, 2.4 ml of pyridine and 5 ml of chloroform was added while cooling. After standing for 1 hour at room temperature, the mixture was washed twice with water, and the solvent was evaporated in vacuo. The resinous residue, which was uniform according to thin-layer chromatography and consisted of 2-chloro-1-(3-methoxyphenyl)-indole 3-carboxylic acid (4-methyl)-piperazide, was dissolved in 40 ml of diglym, and after addition of 13 g (0.15 mol) of piperazine, the solution was heated to the boil. The cooled solution was diluted with methylene chloride, washed three times with water, and the solvent was eliminated in vacuo. The resinous residue was dissolved in chloroform, and an excess of ethanolic hydrochloric acid was added. The solvent was eliminated in vacuo, the crystallized residue was digested with acetone, suction-filtered and washed with acetone. The yield of faintly grey-colored dihydrochloride of the above compound amounted to 3.7 g (73% of the theoretical yield), m.p. 228°-230° C.

후처리

  1. temperaturewhile cooling
  2. washthe mixture was washed twice with water
  3. customthe solvent was evaporated in vacuo
  4. dissolutionwas dissolved in 40 ml of diglym
  5. temperaturethe solution was heated to the boil
  6. washwashed three times with water
  7. dissolutionThe resinous residue was dissolved in chloroform
  8. additionan excess of ethanolic hydrochloric acid was added
  9. filtrationsuction-filtered
  10. washwashed with acetone
  11. customtheoretical yield), m.p. 228°-230° C.

출처 및 근거

ORD 기록
ord-2c8b5b82730646d2bf426bb8c3202b96
출처 데이터셋
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04148895

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