Réaction #70490

Équation de réaction

6-[4-(4-benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridine-3-carbaldehyde

NaBH(OAc)3

morpholine

NaHCO3

→

title compound

Rendement 80.0%

1-Benzyl-4-[4-(5-morpholin-4-ylmethyl-pyridin-2-yl)-piperazin-1-yl]-phthalazine

Rendement 80.0%

Solvants

DCM

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture is stirred for an additional 30 min
2. 2
   AutreThe layers are separated
3. 3
   Extractionthe aqueous layer is extracted with DCM
4. 4
   LavageThe combined organic layers are washed with water, brine
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude product is purified by flash chromatography on silica gel (EtOAc/heptane 10%-70%)

Mode opératoire

To a solution of 6-[4-(4-benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridine-3-carbaldehyde (40 mg, 0.1 mmol) in 5 mL DCM is added a drop of acetic acid, NaBH(OAc)3 (41.4 mg, 0.2 mmol) and morpholine (7.5 mL, 0.12 mmol). The reaction mixture is stirred for 30 min at rt. Aqueous NaHCO3 solution is added and the reaction mixture is stirred for an additional 30 min. The layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography on silica gel (EtOAc/heptane 10%-70%) to yield the title compound (37.8 mg, 80%).

Source