1-Amino-2-propanol → 1-((4-Chlorophenethyl)amino)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

Into a 1-L jacketed reactor equipped with a retreat curve stir blade, overhead stirring, a thermocouple, a condenser, and a nitrogen bubbler was charged 1-aminopropan-2-ol (110 mL, 1430 mmol), which was then heated to 85 and 90° C. 1-Chloro-4-(2-chloroethyl)benzene (50.054 g, 286 mmol) was charged via addition funnel over 1 h with a maximum reaction temperature of 93° C. Stirring was then continued at 90 to 95° C. for 2.5 h. Chlorobenzene (100 mL) and water (50 mL) were added and the mixture was stirred at 70 to 75° C. for 15 min. The phases were allowed to separate and the aqueous phase was extracted with chlorobenzene (2×50 mL) at 70 to 75° C. The combined organic phases were then washed with water (2×50 mL) at 70 to 75° C. and concentrated by distillation under reduced pressure. The residue was dissolved in chlorobenzene to a total weight of 503 g and allowed to stand at room temperature overnight. A solid precipitate formed which was redissolved by adding chlorobenzene (50 mL) and heating the mixture at 30 to 35° C.

Provenance & Evidence