Diethyl Ether → 4-(Chloropropyl)-1-(2-quinolyl)piperazine

HRID 1714760Notes

Reaction equation

HRID 1714760 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23].C(OCC)C>CC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5011QuipazineHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide

Product 1

HCID 30355894-(Chloropropyl)-1-(2-quinolyl)piperazineYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolving 853 mg of 2-piperazin-1-ylquinoline as prepared in above Step 1-1-A in 5 ml of acetone, 5 ml of an aqueous solution containing 160 mg of sodium hydroxide was added to the solution, and into which 0.5 ml of 1-bromo-3-chloropropane was dropped, followed by stirring for an overnight at room temperature. Then diethyl ether was added, followed by washing with saturated aqueous sodium hydrogencarbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified on silica gel column chromatography (chloroform:methanol=50:1) to provide 1.10 g (95%) of 2-[4-(3-chloropropyl)piperazin-1-yl]quinoline.

Workup

  1. additionwas added to the solution
  2. washby washing with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-5d76bdadd9eb4c478cc72ffa2d0d7166
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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