1-Methylpiperazine → HCID 15345718, compound

HRID 864643Notes

Reaction equation

HRID 864643 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:12]=[C:13](Cl)[N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][CH2:6]3.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:12]=[C:13]([N:19]3[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]3)[N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][CH2:6]3

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 19419847HCID 19419847, compound

Product 1

HCID 15345718HCID 15345718, compoundYield 57%

Procedure

A solution of 7-bromo-2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.00 g) in N-methylpiperazine (20 ml) was stirred under reflux, under nitrogen, for two hrs. The reaction mixture was quenched with dilute 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 gel; 7:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated. The residue was recrystallized from ethyl acetate-ether to give 2.1 g (57%) of product, mp 132°-133° C.

Workup

  1. temperatureunder reflux, under nitrogen, for two hrs
  2. customThe reaction mixture was quenched with dilute 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 gel; 7:1 dichloromethane-methanol)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-7f17b67110bc40968aaa746cf6be8a05
Source dataset
uspto-grants-1996_10
Patent number
US05563272

Reaction notes

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