Réaction #68225

Équation de réaction

hydrogen chloride ethyl acetate

sodium hydrogen carbonate

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-4-(pyridin-4-yl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

trifluoroacetic acid

→

1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-4-(pyridin-4-yl)quinolin-2(1H)-one hydrochloride

Solvants

chloroform

chloroform

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   Autrethe solvent was removed under reduced pressure
3. 3
   AutreTo the residue thus obtained
4. 4
   Autrethe organic layer was separated
5. 5
   Extractionthe aqueous layer was extracted with chloroform
6. 6
   Lavagewashed with aqueous saturated sodium chloride solution
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Autrethe solvent was removed under reduced pressure
9. 9
   AutreTo the residue thus obtained
10. 10
    Filtrationthe resulting solid was filtered

Mode opératoire

To 1 mL of a chloroform solution containing 42 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(2-oxo-4-(pyridin-4-yl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 1 mL of trifluoroacetic acid was added at room temperature and stirred for 3.5 hours, thereafter the solvent was removed under reduced pressure. To the residue thus obtained, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, 1 mL of 4 mol/L hydrogen chloride/ethyl acetate was added, the resulting solid was filtered to give 21 mg of (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-4-(pyridin-4-yl)quinolin-2(1H)-one hydrochloride as a pale yellow solid.

Source