Reaction #70490

Reaction equation

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

NaBH(OAc)3

morpholine

NaHCO3

→

title compound

Yield 80.0%

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

Yield 80.0%

Solvents

DCM

acetic acid

Conditions

Workup

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

Procedure

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