Reacción #68084

Ecuación de reacción

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

Rendimiento 64.8%

Disolventes

acetic acid

water

chloroform

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente