Sulfuric Acid → 2-(1-Piperazinylmethyl)quinoline

HRID 365299Notes

Reaction equation

HRID 365299 reaction equation
C([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:5][CH2:4]1)=O.S(=O)(=O)(O)O>C(O)C>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[CH2:9][N:6]1[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 23291104HCID 23291104, compound

Product 1

HCID 43753132-(1-Piperazinylmethyl)quinolineYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Formyl-4-(2-quinolylmethyl)piperazine (86.00 g, 332 mmol) was dissolved in ethanol (800 ml), followed by the addition of concentrated sulfuric acid (49.04 g, 500 mmol). After the resulting mixture was heated under reflux and stirring for 4 days, the solvent was distilled off under reduced pressure. The thus-obtained residue was dissolved in water. After the resulting solution was washed twice with chloroform, the solution was rendered basic with a 10N aqueous solution of sodium hydroxide, followed by extraction with chloroform. The extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby 73.65 g of the title compound were obtained as a pale amber oil (yield: 97.6%).

Workup

  1. temperatureAfter the resulting mixture was heated
  2. temperatureunder reflux
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe thus-obtained residue was dissolved in water
  5. washAfter the resulting solution was washed twice with chloroform
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1ab05e3939d94080a4f1b91af98ff042
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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