Reaction #68061

Reaction equation

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-4-((methylamino)carbonyl)-2-oxoquinolin-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)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

Yield 70.3%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe solvent was removed under reduced pressure, chloroform and water
3. 3
   workup.ADDITIONwere added
4. 4
   OtherThe organic layer was separated
5. 5
   Extractionthe aqueous layer was extracted with chloroform
6. 6
   Washwashed with aqueous saturated sodium chloride solution
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Otherthe solvent was removed under reduced pressure

Procedure

To 2 mL of a dichloromethane solution containing 0.15 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-4-((methylamino)carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 2 mL of trifluoroacetic acid was added and stirred at room temperature for 30 min. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 11 with 20% aqueous sodium hydroxide solution. 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 give 88 mg of 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide as a pale yellow foam.

Source