تفاعل #68227

معادلة التفاعل

sodium cyanoborohydride

methanol

1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

2-naphthoaldehyde

→

7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide

المردود 119.6%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at the same temperature for 75 min
3. 3
   أخرىAfter the solvent was removed under reduced pressure, chloroform and aqueous saturated sodium hydrogen carbonate solution
4. 4
   workup.ADDITIONwere added
5. 5
   أخرىthe organic layer was separated
6. 6
   استخلاصthe aqueous layer was extracted with chloroform
7. 7
   غسيلwashed with aqueous saturated sodium chloride solution
8. 8
   تجفيفdried over anhydrous magnesium sulfate
9. 9
   أخرىthe solvent was removed under reduced pressure
10. 10
    أخرىThe residue thus obtained
11. 11
    أخرىwas purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1]

الإجراء التجريبي

To 4 mL of a methanol solution containing 0.14 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide, 55 mg of 2-naphthoaldehyde and 40 μL of acetic acid were added, and stirred at room temperature for 80 min. To the reaction mixture, 52 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 75 min. After the solvent was removed under reduced pressure, 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. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; chloroform:methanol=30:1], to give 0.21 g of 7-methoxy-N-methyl-1-(2-(4-((naphthalen-2-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxamide as a yellow foam.

المصدر