تفاعل #68130

معادلة التفاعل

4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile

(2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde

(2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde

sodium hydrogen carbonate

sodium cyanoborohydride

→

1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile

المردود 80.1%

المذيبات

dichloromethane

methanol

dichloromethane

acetic acid

chloroform

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.STIRRINGstirred 1 hour and 50 min
3. 3
   workup.ADDITIONwas further added
4. 4
   workup.STIRRINGstirred for 1 hour
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 flash silica gel column chromatography[gradient elution of chloroform

الإجراء التجريبي

To 5 mL of methanol solution containing 0.20 g of 4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile, 1.5 mL of dichloromethane solution containing 0.33 g of (2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde and 70 μL of acetic acid were added at room temperature, and stirred at the same temperature for 55 min. 77 mg of sodium cyanoborohydride was added at room temperature, and stirred 1 hour and 50 min, thereafter 0.5 mL of dichloromethane solution containing 0.10 g of (2,3-dihydrobenzo[b](1,4)dioxin-6-yl)acetaldehyde was further added and stirred for 1 hour. To the reaction mixture, water, 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, thereafter dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography[gradient elution of chloroform:methanol=99:1-97:3], to give 0.24 g of 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-4-carbonitrile as a white foam.

المصدر