Phthalic Anhydride → HCID 178465696, compound

Participants

Reaction Steps

A mixture of 702 mg (1.63 mmol) [trans-(2-(4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-cyclohexyl)-ethyl]-methyl-carbamic acid 4-trifluoromethyl-phenyl ester, 256.6 mg (1.8 mmol) of phthalic anhydride and 335 mg (3.54 mmol) of Hydrogen peroxide•Urea adduct in 7 ml of CH2Cl2, was stirred for two days at RT. Additional 100 mg (1.06 mmol) of Hydrogen peroxide•Urea adduct and 50 mg (0.34 mmol) of phthalic anhydride were added to the reaction mixture. After another 3 h at RT, 10 ml of aqueous saturated NaHCO3 were added. After stirring for 10 min at RT, the reaction-mixture was taken up in ether/water. The ether phase was dried and evaporated under reduced pressure. The residue was chromatographed on silica gel with a 9:1 v/v mixture of methylenchloide/methanol as eluent giving 449 mg (62%) of pure rac-trans-ethyl(2-hydroxyethyl)({4-[2-(methyl{[4-(trifluoromethyl)phenoxy]carbonyl}amino)ethyl]cyclohexyl}methyl)ammoniumolate, MS: 447 (MH+).

Provenance & Evidence