Piperazine → Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate

HRID 862650Notes

Reaction equation

HRID 862650 reaction equation
Cl[CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CO>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([C:11]2[C:10]3[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=3)[N:4]=[C:3]([CH2:2][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 22097621Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylateYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.0 g), piperazine (1.15 g) and methanol (15 ml) was stirred at room temperature for 36 hours. The reaction mixture was concentrated under reduced pressure, and 6N HCl (30 ml) was added to the residue. The resulting mixture was washed with dichloromethane. The aqueous layer was neutralized with 2N NaOH and extracted with dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated. The crystals were collected by filtration and recrystallized from dichloromethane-hexane to give ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-piperazinomethylquinoline-3-carboxylate (0.43 g, 39%). Colorless prisms. mp. 192°-193° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 6N HCl (30 ml)
  2. additionwas added to the residue
  3. washThe resulting mixture was washed with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. filtrationThe crystals were collected by filtration
  9. customrecrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-7f8ef0aad6964b348d074d83f717f03d
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

Loading…