Réaction #68084

Équation de réaction

sodium triacetoxyborohydride

dichloromethane

ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)piperazine-2-carboxylate

(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

→

ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate

Rendement 64.8%

Solvants

acetic acid

water

chloroform

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   Autrethe organic layer was separated
4. 4
   Extractionthe aqueous layer was extracted with chloroform
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Autrethe solvent was removed under reduced pressure
7. 7
   AutreThe residue thus obtained
8. 8
   Autrewas purified by silica gel column chromatography [eluent; chloroform: acetone=50:1]

Mode opératoire

To 2.5 mL of dichloromethane solution containing 0.14 g of ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)piperazine-2-carboxylate and 0.10 g of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 25 μL of acetic acid were added and stirred at room temperature for 50 min. Then, 0.14 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 1 hour. To the reaction mixture, chloroform and water were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform: acetone=50:1], to give 0.15 g of ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate as a colorless foam.

Source