Hydrochloric Acid → 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide

2-{3-[4-(2-Methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.21 g, 0.53 mmol), prepared as in Example 21, was dissolved in methylene chloride and the solution was treated with excess hydrochloric acid in methanol and concentrated under reduced pressure. The residue was dissolved in 6 mL of DMF and N-bromosuccinimide (0.101 g, 0.57 mmol) was added. The mixture was stirred at room temperature for approximately 24 hours, diluted with water and basified with K2CO3. The basified mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified on silica gel by column chromatography eluting with 5% methanol/methylene chloride to give 2-{3-[4-(4-bromo-2-methoxyphenyl)piperazin-1-yl]propylamino}-N,N-dimethylnicotinamide (0.19 g, 0.40 mmol) as an oil.

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in 6 mL of DMF
3. extractionThe basified mixture was extracted with ethyl acetate
4. washthe ethyl acetate layer was washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified on silica gel by column chromatography
9. washeluting with 5% methanol/methylene chloride

ORD-Eintrag

ord-d495feaf3efc471bb2cd5223249bbbe7

Quelldatensatz

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05688795