Réaction #161743

Équation de réaction

2-chloro-6-methoxyquinoline

lithium diisopropylamide

THF

THF

N-benzylpiperidone

→

1-benzyl-4-(2-chloro-6-methoxy-quinolin-3-yl)-piperidin-4-ol

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred for a further 15 min
2. 2
   Températurewith cooling
3. 3
   Températurebefore slowly being heated to RT
4. 4
   workup.STIRRINGThe reaction mixture was stirred overnight
5. 5
   Autreevaporated down
6. 6
   Autrepurified by flash chromatography on aluminium oxide
7. 7
   Autreevaporated down

Mode opératoire

Under an argon atmosphere 5.0 g (25 mmol) 2-chloro-6-methoxyquinoline in a small amount of THF were added dropwise at −78° C. to 14 mL (28 mmol) of a 2 M lithium diisopropylamide solution (in THF) in 50 mL THF. Then the mixture was stirred for 1.5 h at −78° C. and 4.5 mL (25 mmol) N-benzylpiperidone was added dropwise. The mixture was stirred for a further 15 min with cooling before slowly being heated to RT. The reaction mixture was stirred overnight, evaporated down and purified by flash chromatography on aluminium oxide. The product-containing fractions were combined and evaporated down.

Source