Triethylamine → 1-{1-[4-(3,4-Dichloro-benzoyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea

Participants

Reaction Steps

A solution of [1-(2-amino-3-methylbutyl)piperidin-4-yl]-(3,4-dichlorophenyl)methanone (30 mg) in dichloromethane (3 mL) was treated with trimethoxyphenyl-isocyanate (30 mg) and triethylamine (1 mL, 0.3 M in dichloromethane) was added and the reaction mixture was stirred at ambient temperature overnight. A polystyrene trisamine resin (approx. 0.5 g, 3.5 mmol/g) was added to capture excess isocyanate, and stirring was continued for an additional 2 h. The resin was filtered and the filtrate was concentrated. Purification by column chromatography gave 1-{1-[4-(3,4-dichloro-benzoyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea (27.5 mg).

Provenance & Evidence