Carbon Dioxide → HCID 22082763, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-morpholinobenzoic acid (0.59 g, 2.8 mmol; described in: Degutis, J.; Rasteikiene, L.; Degutiene, A. Zh. Org. Khim. 1978, 14(10), 2060-2064) in anhydrous N,N-dimethylformamide (30 mL) was added 1,1′-carbonyldiimidazole (0.48 g, 3.0 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 tert-butyl (R)-4-(7-amino-5,6,7,8-tetrahydro-1-naphthyl)piperazine-1-carboxylate (0.90 g, 2.7 mmol) in anhydrous N,N-dimethylformamide (15 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 (100:2) as the eluent gave 1.5 g (84% yield) of the title compound as a dark-red viscous oil: [α]21D −45° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 520 (5, M+).

Provenance & Evidence