1-Methylpiperazine → HCID 19419841, compound

HRID 864644Notes

Reaction equation

HRID 864644 reaction equation
Cl[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]([CH3:14])=[CH:5][C:4]=3[N:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[CH3:14][C:6]1[CH:7]=[C:8]2[C:13]3=[C:4]([N:3]=[C:2]([N:19]4[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]4)[N:12]3[CH2:11][CH2:10][CH2:9]2)[CH:5]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 19419829HCID 19419829, compound

Product 1

HCID 19419841HCID 19419841, compoundYield 76%

Procedure

A solution of 2-chloro-5,6-dihydro-8-methyl-4H-imidazo[4,5,1-ij]quinoline (3.50 g) in N-methylpiperazine (20 ml) was stirred, under nitrogen, under reflux for 1.5 hrs. The reaction mixture was quenched with saturated sodium bicarbonate solution (200 ml) and extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica; 9:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated. The residue was recrystallized from ethyl acetate to give 3.48 g (76%) of product, mp 164°-165° C.

Workup

  1. temperatureunder reflux for 1.5 hrs
  2. customThe reaction mixture was quenched with saturated sodium bicarbonate solution (200 ml)
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by high performance liquid chromatography (silica; 9:1 dichloromethane-methanol)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b56bc3ce4ccf452295a0aeeda90911fb
Source dataset
uspto-grants-1996_10
Patent number
US05563272

Reaction notes

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