Water → 1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (2.6 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.45 g, 80% suspension in oil) in N,N-dimethylformamide (20 cc). After 15 minutes, stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (3.51 g) in N,N-dimethylformamide (10 cc) is added. The reaction mixture is heated to 80° C. for 90 minutes and is then cooled and poured into a mixture of water (100 cc) and ethyl acetate (200 cc). The organic phase is washed with water, is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 50-cm height) with ethyl acetate as eluent and with 125-cc fractions being collected. Fractions 2 to 6 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from ethyl acetate, 1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (3.7 g) is obtained, melting at 120° C.

Herkunft & Nachweise