Reaction #1005985

Reaction equation

2-chloromethylquinoline hydrochloride

potassium carbonate

tert-butyl piperazine-1-carboxylate

→

2-(piperazin-1-ylmethyl)quinoline

Yield 92.0%

Solvents

acetone

Conditions

Workup

1. 1
   OtherReaction
2. 2
   Filtrationfiltered through celite
3. 3
   ConcentrationFiltrate was concentrated on Rotavapor under vacuum
4. 4
   Otherthe crude residue was purified on SiO2 using Biotage SP1

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).

Source