Hydrochloric Acid → HCID 68524422, compound

HRID 884136Notes

Reaction equation

HRID 884136 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][CH2:21][C:22](OCC)=[O:23])[CH:6]=[CH:7][C:8]=1[N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1.[OH-].[Na+].Cl.[CH2:30]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[C:31]1[CH:39]=[CH:38][C:37]2[O:36][CH2:35][O:34][C:33]=2[CH:32]=1>C(O)C.CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][CH2:21][C:22]([N:43]2[CH2:44][CH2:45][N:40]([CH2:30][C:31]3[CH:39]=[CH:38][C:37]4[O:36][CH2:35][O:34][C:33]=4[CH:32]=3)[CH2:41][CH2:42]2)=[O:23])[CH:6]=[CH:7][C:8]=1[N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 944261-PiperonylpiperazineHCID 68525615HCID 68525615, compound

Product 1

HCID 68524422HCID 68524422, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-{3-methoxy-4-[methyl-(5-nitropyridin-2-yl)amino]phenyl}propionate (3.85 g, 11 mmol) in ethanol (80 mL) was added 2 N aqueous sodium hydroxide (6.4 mL, 13 mmol), and the resulting solution was stirred at room temperature for 2.5 hours. To the resulting reaction solution was added 6 N hydrochloric acid (2.2 mL, 13 mmol), and the solvent was removed under reduced pressure. To the residue were added THF (80 mL) and N,N′carbonyldiimidazole (2.08 g, 13 mmol), and the resulting solution was stirred at room temperature for 3 hours. To the resulting reaction solution were added 1-piperonylpiperazine (2.60 g, 12 mmol) and DMF (40 mL), and stirred at room temperature for 21 hours. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate), to thereby yield 4.59 g of the title compound.

Workup

  1. customTo the resulting reaction solution
  2. customthe solvent was removed under reduced pressure
  3. stirringthe resulting solution was stirred at room temperature for 3 hours
  4. customTo the resulting reaction solution
  5. stirringstirred at room temperature for 21 hours
  6. customThe solvent was evaporated under reduced pressure
  7. extractionthe residue was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dc921f1076ed4ea1a903ef11aa690879
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

Loading…