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Piperazine → 1,6-Dimethyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile

HRID 346599
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HRID 346599 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]#[N:16].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>ClCCl>[CH3:13][N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:2]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[C:3]([C:15]#[N:16])[C:4]1=[O:14]
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참가 물질

4

반응물 2

HCID 4837PiperazineHCID 210819594-Chloro-1,6-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

생성물 1

HCID 210819011,6-Dimethyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile수율 88.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of Compound 23 (1 g, 4.3 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (1.1 g, 12.9 mmol) in dichloromethane at room temperature. The solution was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was taken in water, sonicated briefly, and filtered. The solids were dissolved in ethyl acetate and washed by water. The organic layer was dried over Na2SO4 and concentrated to yield 1.07 g (88%) yellow solids. M.P. 274° C. 1H NMR (DMSO-d6): δ 2.39 (s, 3H), 2.94 (m, 4H), 3.48 (m, 4H), 3.54 (s, 3H), 7.45 (d, J=8.6 Hz, 1H), 7.56 (dd, J=1.3, 8.6 Hz, 1H), 7.64 (s, 1H). EIMS m/z 283 (M+1).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customsonicated briefly
  3. filtrationfiltered
  4. dissolutionThe solids were dissolved in ethyl acetate
  5. washwashed by water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-56be600f4e5044d59ba275d33a254d3c
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173036B2

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