Potassium Carbonate → N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]acetyl}phenyl)acetamide

HRID 734555Notes

Reaction equation

HRID 734555 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15](CCC3C=C(C=CC=3)N)[CH2:14][CH2:13]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:34][C:35]([C:37]1[CH:38]=[C:39]([NH:43][C:44](=[O:46])[CH3:45])[CH:40]=[CH:41][CH:42]=1)=[O:36]>CN(C=O)C.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:34][C:35]([C:37]3[CH:38]=[C:39]([NH:43][C:44](=[O:46])[CH3:45])[CH:40]=[CH:41][CH:42]=3)=[O:36])[CH2:14][CH2:13]2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21115378N-[3-(2-chloroacetyl)phenyl]acetamideHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Product 1

HCID 57444326N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]acetyl}phenyl)acetamideYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2-methyl-5-(1-piperazinyl)quinoline (D6, 0.14 g, 1 eq) in dry DMF (5 mL) were added potassium carbonate (0.11 g, 1.2 eq) and a solution of N-[3-(2-chloroacetyl)phenyl]acetamide (J. Chem. Soc., 1949, 552, 553, 0.17 g, 1.2 eq) in DMF (3 mL) under an inert atmosphere. The reaction was stirred for 1.5 hrs. The mixture was diluted with water (8 mL) and extracted with DCM (3×15 mL). The organic phase was washed with brine (25 mL), dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) using as eluant DCM-methanol (95:5), affording the title compound in 42% yield (0.104 g).

Workup

  1. extractionextracted with DCM (3×15 mL)
  2. washThe organic phase was washed with brine (25 mL)
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude material was purified on SPE cartridge (Silica)

Sources & evidence

ORD record
ord-f99ae8c397eb498389cca577b1a9bc67
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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