Methylparaben → N,N-Diisopropyl-3-[(5-methoxycarbonyl)-2-hydroxy)phenyl]-3-phenyl-propylamine

Participants

Reaction Conditions

Reaction Steps

Methyl 4-hydroxy-benzoate (52.0 g, 340 mmol) is suspended in methanesulfonic acid (90 ml) in a round-bottom flask under inert atmosphere and the mixture is heated at a temperature of 50-55° C. 3-Diisopropylamino-1-phenyl-propan-1-ol (20.0 g, 85.0 mmol) is slowly added in about 2 hours and the mixture is reacted while hot for 5-6 hours. The mixture is cooled at room temperature and slowly poured in ice/water (200 g) under strong stirring. The product is extracted with dichloromethane (200 ml) and the organic phase is washed with a 10% sodium hydroxide solution (2×100 ml), then with an ammonium chloride aqueous solution until neutral pH. 28.9 g of a product are obtained in 92% yield.

Provenance & Evidence