Carbon Dioxide → 3-Methyl-4-(4-morpholinyl)-N-[(2R)-1,2,3,4-tetrahydro-8-(4-methyl-1-piperazinyl)-2-naphthalenyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-4-morpholinobenzoic acid (110 mg, 0.51 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1,1′-carbonyldiimidazole (87 mg, 0.54 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 (120 mg, 0.49 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at ambient temperature for 15 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/ethanol saturated with NH3 (100:2) as the eluent gave 110 mg (50% yield) of the title compound as white crystals: mp 172-175° C.; [α]21D '47° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 448 (5, M+).

Provenance & Evidence