Potassium Carbonate → 2-(1-Piperazinylmethyl)quinoline

HRID 918803Notes

Reaction equation

HRID 918803 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(=O)([O-])[O-].[K+].[K+].[N:20]1(C(OC(C)(C)C)=O)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CC(C)=O>[N:20]1([CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 43753132-(1-Piperazinylmethyl)quinolineYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-chloromethylquinoline hydrochloride (5 mmol) in anhydrous acetone (100 mL) was added, anhydrous potassium carbonate (15 mmol) and tert-butyl piperazine-1-carboxylate (7 mmol) and the reaction mixture was stirred under reflux conditions for 12 h. Reaction was cooled to r.t. and filtered through celite. Filtrate was concentrated on Rotavapor under vacuum and the crude residue was purified on SiO2 using Biotage SP1 to give a pure 2-(piperazin-1-ylmethyl)quinoline (6.3, 92%, pale yellow solid).

Workup

  1. customReaction
  2. filtrationfiltered through celite
  3. concentrationFiltrate was concentrated on Rotavapor under vacuum
  4. customthe crude residue was purified on SiO2 using Biotage SP1

Sources & evidence

ORD record
ord-59e75fae0a35430d88a99ccc0ac45941
Source dataset
uspto-grants-2016_03
Patent number
US09271962B2

Reaction notes

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