1-(Ethanesulfonyl)piperazine → 4-(Ethylsulfonyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexan-amine

HRID 542853

반응식

HRID 542853 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[C:11]([O:20][CH3:21])[CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[C:14]2[CH3:19].[CH2:22]([S:24]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(=[O:26])=[O:25])[CH3:23]>ClCCl.O>[CH2:22]([S:24]([N:27]1[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:10]=[C:11]([O:20][CH3:21])[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[C:14]3[CH3:19])[CH2:31][CH2:32]1)(=[O:26])=[O:25])[CH3:23]

참가 물질

5

반응물 2

HCID 4152941-(Ethanesulfonyl)piperazineHCID 608631N-[6-Chlorohexyl]-6-methoxy-4-methyl-8-quinolinamine

생성물 1

HCID 130775494-(Ethylsulfonyl)-N-(6-methoxy-4-methyl-8-quinolinyl)-1-piperazinehexan-amine수율 68.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1.5 g. (0.0049 mole) of N-(6-chlorohexyl)-6-methoxy-4-methyl-8-quinolinamine and 2.7 g (0.015 mole) of 1-(ethylsulfonyl)-piperazine was heated at 130° for 50 min, allowed to cool and taken up in dichloromethane and water. The organic layer was washed again, dried, and concentrated to dryness in vacuo. The residue was chromatographed over 70 g of silica gel first with ethyl acetate and then with 2% methanol in ethyl acetate. The eluant containing product, Rf(silica--ethyl acetate)=0.05, was concentrated to dryness in vacuo. Recrystallization of the residue from 2-propanol afforded 1.5 g (68%) of the title compound, mp 72°-74°.

후처리

  1. additionA mixture of 1.5 g
  2. temperatureto cool
  3. washThe organic layer was washed again
  4. customdried
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue was chromatographed over 70 g of silica gel first with ethyl acetate
  7. additionThe eluant containing product, Rf(silica--ethyl acetate)=0.05
  8. concentrationwas concentrated to dryness in vacuo
  9. customRecrystallization of the residue from 2-propanol

출처 및 근거

ORD 기록
ord-6f7c61972ac14997be44619fa524bffa
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659708

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