Sulfuric Acid → HCID 58557779, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL flask, ethyl 4-(dibenzylamino)cyclohexanecarboxylate (7.2 g, 20.5 mmol) and a solution of conc. H2SO4 (7.64 mL, 143 mmol) in water (80 mL) were added. The reaction mixture was stirred at about 90° C. for about 18 h, cooled to about 5° C. and the pH was adjusted to about 7 with the addition of 50% aqueous NaOH. The aqueous solution was extracted with ether (300 mL). The organic layer was dried over anhydrous Na2SO4, filtered and washed with ether. The filtrate was concd under reduced pressure to give 4-(dibenzylamino)cyclohexanecarboxylic acid (5.6 g, 85%) as a solid: LC/MS (Table 1, Method b) Rt=1.65 min; MS m/z: 324 (M+H)+.

Provenance & Evidence