1-Methylpiperazine → 5-chloro-3-(4-methoxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dione

HRID 735265Notes

Reaction equation

HRID 735265 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:14])[C:6](=[O:13])[NH:7]2.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:11]=[C:10]([N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:14])[C:6](=[O:13])[NH:7]2

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 116746945,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 115606535-chloro-3-(4-methoxy-phenyl)-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dioneYield 32%

Procedure

A mixture of 5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.10 g, 0.29 mmol) and 1-methylpiperazine (3.0 mL) was heated at reflux temperature overnight. Excessive 1-methylpiperazine was removed by evaporation in vacuo. The residue was diluted with water (50 mL), and resulting suspension was extracted with ethyl acetate (50 mL×3). The organic layer was washed with brine (50 ml×2), dried over anhydrous MgSO4, and concentrated under reduced pressure. The pure objective compound (38 mg, 32%) was obtained as yellow solid by a flash column chromatography (CH2Cl2:MeOH=20:1): 1H NMR (200 MHz, CDCl3) δ 1.82 (s, 3H, CH3), 2.33 (s, 3H, NCH3), 2.44-2.65 (m, 4H, 2×NCH2), 2.88-2.91 (m, 4H, 2×NCH2), 3.74 (s, 3H, OCH3), 6.43 (d, J=1.8 Hz, 1H, ArH) 6.54 (d, J=1.8 Hz, 1H, ArH), 6.80 (d, J=9.0 Hz, 1H, ArH), 7.19 (d, J=9.0 Hz, 1H, ArH), 9.23 (s, 1H, NH); m.p. 201-202° C.; MS(EI) m/e 413 [M+]; HRMS m/e cacld. for C22H24N3O3Cl1 413.1506, found 413.1516.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. customExcessive 1-methylpiperazine was removed by evaporation in vacuo
  4. additionThe residue was diluted with water (50 mL)
  5. customresulting suspension
  6. extractionwas extracted with ethyl acetate (50 mL×3)
  7. washThe organic layer was washed with brine (50 ml×2)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-163fe90631c64e8882d7b8de6f02d6f4
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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