Water → HCID 57445001, compound

Participants

Reaction Steps

A solution of 3-(morpholinomethyl)aniline (0.46 g), TEA (0.37 mL) and 4-nitrophenyl carbonochloridate (530 mg) in THF (18 mL) was stirred at ambient temperature for 2 hours, treated with tert-butyl 4-aminophenylcarbamate (500 mg) and an additional 0.37 mL of TEA. the resulting mixture was stirred at ambient temperature for 48 hours, poured into water and extracted 3× with ethyl acetate. The extract was washed with brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel with 2% methanol/dichloromethane to provide 1-(3-(morpholinomethyl)phenyl)-3-(4-nitrophenyl)urea which was dissolved in dichloromethane (30 mL), cooled in an ice bath, and treated with TFA (1.8 mL). The reaction mixture was stirred for 30 minutes at 0° C. and for 12 hours at ambient temperature, and concentrated three times from methanol/toluene.

Provenance & Evidence