Réaction #84094

Équation de réaction

2-chloro-6-methoxy-3-(trifluoromethyl)quinoline

Intermediate 6

2-chloro-6-methoxy-3-(trifluoromethyl)quinoline

methyl-4-piperidinecarboxylate

Et3N

→

product

Rendement 43.0%

methyl 1-(6-methoxy-3-(trifluoromethyl)quinolin-2-yl)piperidine-4-carboxylate

Rendement 43.0%

Solvants

IPA

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureto reflux for 48 hours
3. 3
   Extractionextracted with DCM (100 mL×3)
4. 4
   Lavagethe combined organic layers were washed with brine (200 mL)
5. 5
   Séchagedried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Autreto give the crude product, which
9. 9
   Autrewas purified by column chromatography on silica gel (PE/EtOAc=15/1)

Mode opératoire

To a solution of 2-chloro-6-methoxy-3-(trifluoromethyl)quinoline (1.00 g, 3.85 mmol) (see Intermediate 6, Step 8 for synthesis) in IPA (5 mL) was added methyl-4-piperidinecarboxylate (5.50 g, 38.5 mmol) and Et3N (1.17 g, 11.6 mmol). The mixture was heated to reflux for 48 hours. The mixture was diluted with water (100 mL) and extracted with DCM (100 mL×3), the combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (PE/EtOAc=15/1) to give the product (600 mg, yield 43%) as a solid.

Source