反応 #68130

反応方程式

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

収率 80.1%

溶媒

dichloromethane

methanol

dichloromethane

acetic acid

chloroform

water

反応条件

後処理

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
   その他the organic layer was separated
6. 6
   抽出the aqueous layer was extracted with chloroform
7. 7
   洗浄washed with aqueous saturated sodium chloride solution
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   その他the solvent was removed under reduced pressure
10. 10
    その他The residue thus obtained
11. 11
    その他was purified by flash silica gel column chromatography[gradient elution of chloroform

実験手順

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.

出典