1-Piperazinecarboxaldehyde → 4-[5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl]-1-piperazinecarboxaldehyd

HRID 1440705Notes

Reaction equation

HRID 1440705 reaction equation
Cl[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.[N:14]1([CH:20]=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>>[N:3]1[C:4]2=[C:13]3[C:8](=[CH:7][CH:6]=[CH:5]2)[CH2:9][CH2:10][CH2:11][N:12]3[C:2]=1[N:17]1[CH2:18][CH2:19][N:14]([CH:20]=[O:21])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 821911-PiperazinecarboxaldehydeHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 194198384-[5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2-yl]-1-piperazinecarboxaldehydYield 64.5%

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (20.00 g) in 1-piperazinecarboxaldehyde (25.00 g) was stirred at 120° C., under nitrogen, for 1.5 hrs. The reaction mixture was quenched with dilute sodium bicarbonate solution (300 ml) and extracted with chloroform. The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated. The residue was purified by flash chromatography (silica gel; 25:1 dichloromethane-methanol). The appropriate fractions were collected and evaporated. The residue was recrystallized twice from ethyl acetate to give 18.1 g (64%) of product, mp 138°-139° C.

Workup

  1. customThe reaction mixture was quenched with dilute sodium bicarbonate solution (300 ml)
  2. extractionextracted with chloroform
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by flash chromatography (silica gel; 25:1 dichloromethane-methanol)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-1114f059c1ea4e69ba7780c4c44ca06e
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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