Carbon Dioxide → (R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-(N,N-dipropylaminosulphonyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(N,N-dipropylaminosulphonyl)benzoic acid (120 mg, 0.43 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added 1,1′-carbonyldiimidazole (73 mg, 0.45 mmol) and the reaction was heated at 75° C. When the carbon dioxide evolution had ceased (after 30 min), the reaction was cooled to room temperature and a solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (100 mg, 0.41 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at ambient temperature for 24 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent gave 58 mg (27% yield) of the title compound as a viscous oil: [α]21D −370 (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 512 (11, M+).

Provenance & Evidence