Morpholine → 4-((Morpholin-4-yl)methyl)benzonitrile

To a stirred suspension of 4-(bromomethyl)benzonitrile (4.00 g, 20 mmol) in DCM (50 ml), at room temperature, triethylamine (4.12 g, 41 mmol) and morpholine (2.67 g, 31 mmol) were added. The reaction mixture was stirred overnight at room temperature. The solution was then diluted with DCM (100 ml) and washed with NaHCO3 saturated aqueous solution (50 ml), the organic phase was separated, dried over magnesium sulphate and solvents evaporated under reduced pressure. The product was purified by column chromatography using a 80 g silica gel cartridge and the following gradient: Solvent A: DCM, Solvent B: MeOH, 1 min hold at 100% A followed by 12 min ramp to 2.5% B and then 5 min hold at 2.5% B. The desired fractions were combined and concentrated to dryness under reduced pressure to obtain the desired product as a white solid (3 g, 14.8 mmol, Yield 72%).

1. washwashed with NaHCO3 saturated aqueous solution (50 ml)
2. customthe organic phase was separated
3. dry with materialdried over magnesium sulphate and solvents
4. customevaporated under reduced pressure
5. customThe product was purified by column chromatography
6. customMeOH, 1 min
7. waitfollowed by 12 min ramp to 2.5% B
8. custom5 min
9. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-81417da16c684df18aea44afe691771e

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115088B2