N,N-Dimethylaniline → HCID 19776529, compound

Participants

Reaction Steps

Trichloromethyl chloroformate (3.54 mL, 29.4 mmol) is added dropwise under a nitrogen atmosphere to a solution of 2-phenylphenol (10.0 g, 58.8 mmol) in 150 mL of benzene at room temperature. After the addition, dimethylaniline (7.45 mL, 58.8 mmol) is added dropwise at such a rate that the temperature of the reaction mixture is maintained between 20°-25° C. The resulting mixture is stirred at room temperature for 3 hours. A solution of 4-methylpiperidine (6.95 mL, 58.8 mmol) and dimethylaniline (7.45 mL, 58.8 mmol) in 50 mL of benzene is then added dropwise. After the addition the reaction is stirred at room temperature overnight. The reaction mixture is washed with 1N HCl, 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure. Purification of the crude reaction product by HPLC (hexane-methylene chloride) followed by recrystallization from diisopropyl ether gives the title compound as a white crystalline solid (10.8 g, 62%), mp 85° -86° C.

Provenance & Evidence