Acetic Acid → 2-Methoxy-4-piperazin-1-yl-quinoline

HRID 333926

Reaction equation

HRID 333926 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[C:20](O)(=[O:22])C>COCCCOCCCO>[CH3:20][O:22][C:4]1[CH:3]=[C:2]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4837PiperazineHCID 2283484-Chloro-6-methoxyquinoline

Product 1

HCID 668358742-Methoxy-4-piperazin-1-yl-quinolineYield 66%

Reagents, catalysts & solvents 1

HCID 669843-(3-Methoxypropoxy)-1-propanolSolvent

Procedure

A mixture of 4-chloro-6-methoxyquinoline (0.97 g, 5 mmol), piperazine (4.3 g, 50 mmol) and glacial acetic acid (0.3 ml) was heated under reflux with stirring in dipropyleneglycolmonomethylether for 48 hours. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure and the raw product was purified by column chromatography on a silica column using ethyl acetate and methanol with the addition of 0.1% NH3 to yield 0.85 g of a brown solid (3.3 mmol, 66%). MS (ES) m/z=243.8 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customthe raw product was purified by column chromatography on a silica column
  6. additionwith the addition of 0.1% NH3

Sources & evidence

ORD record
ord-0a32e3b91e724d319bc86de297094ebc
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

Loading…