Reaction #68148

Reaction equation

sodium hydrogen carbonate

methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxylate

1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine

sodium triacetoxyborohydride

→

methyl 1-(2-(1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamino)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

Yield 70.5%

Solvents

acetic acid

chloroform

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred for 0.5 hours
3. 3
   Otherthe organic layer was separated
4. 4
   WashThe organic layer was washed with aqueous saturated sodium chloride solution
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Otherthe solvent was removed under reduced pressure
7. 7
   OtherThe residue thus obtained
8. 8
   Otherwas purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=3:1]

Procedure

To 10 mL of a chloroform solution containing 111 mg of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-4-carboxylate and 93 mg of 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamine, 23 μL of acetic acid was added and stirred at room temperature for 1 hour. To the reaction mixture, 132 mg of sodium triacetoxyborohydride was added and stirred for 0.5 hours. Aqueous saturated sodium hydrogen carbonate solution was added and the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=3:1], to give 134 mg of methyl 1-(2-(1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-ylamino)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate.

Source