Piperazine → Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate

HRID 266131노트

반응식

HRID 266131 반응식
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CO>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

생성물 1

HCID 22097621Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate수율 39%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.0 g), piperazine (1.15 g) and methanol (15 ml) was stirred at room temperature for 36 hours. The reaction mixture was concentrated under reduced pressure, 6N hydrochloric acid (30 ml) was added to the residue, and the mixture was washed with dichloromethane. The aqueous layer was neutralized with 2N sodium hydroxide, and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The residual crystals were separated by filtration, and then recrystallized from dichloromethane-hexane to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate (0.43 g, 39%). Colorless prisms, mp. 192°-193° C.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 6N hydrochloric acid (30 ml)
  2. additionwas added to the residue
  3. washthe mixture was washed with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residual crystals were separated by filtration
  9. customrecrystallized from dichloromethane-hexane

출처 및 근거

ORD 기록
ord-cca11ca634f94b93b1a5b714bb54b0f4
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650410

반응 노트

불러오는 중…