Diisopropylethylamine → 1-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-pyrrolidinone

Temperature

100 °C

N,N-Diisopropylethylamine (0.23 mL) was added to a solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (0.05 g) and 2-[3-(2-oxo-1-pyrrolidinyl)phenyl]ethyl methanesulfonate (0.071 g) in dimethylformamide (1 mL) and the resulting mixture was heated to 100° C. for 18 hours, then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL), a mixture of water and brine (1:1, 2×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with methanol-ethyl acetate (90:10) affording the title compound in 77% yield (0.07 g).

1. temperaturecooled to room temperature
2. washwashed with water (50 mL)
3. additiona mixture of water and brine (1:1, 2×50 mL) and brine (50 mL)
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe crude was purified by flash chromatography on silica gel
7. washeluting with methanol-ethyl acetate (90:10)

ORD record

ord-ab2a73d614ec448dbd23ae70fa71a9b4

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732600B2