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

HRID 1714794Notes

Reaction equation

HRID 1714794 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.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

7

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 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

In 5 ml of acetone, 853 mg of 2-piperazin-1-ylquinoline as synthesized in Step 7-1-A was dissolved and to which 160 mg of sodium hydroxide as dissolved in 5 ml of water was added. Into the mixed liquid 0.5 ml of 1-bromo-3-chloropropane was dropped, followed by stirring for an overnight at room temperature. After addition of diethyl ether, the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, 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
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-065a03f1c020407aa033be8167fff2c4
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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