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

Temperature

85 °C

In a separate 250-mL round-bottom flask equipped with a magnetic stir bar, a thermocouple, a condenser, and a nitrogen bubbler vented to a caustic scrubber, was charged 1-aminopropan-2-ol (60.1 g, 800 mmol), which was then heated to 85° C. To this was slowly added the toluene solution of 1-chloro-4-(2-chloroethyl)benzene from Step A while maintaining the reaction temperature at <99° C. On completion of the addition, stirring was continued at 90 to 95° C. for 2 h. Toluene (50 mL) and water (25 mL) were added and the mixture was stirred at 70 to 75° C. for 15 minutes before the phases were separated at room temperature. The upper aqueous phase was extracted with toluene (2×25 mL) at 70 to 75° C. Then, the combined organic phases were washed with water (2×25 mL) at 70 to 75° C., and concentrated by distillation under reduced pressure at 60° C. (bath). The residue was diluted with toluene to a total volume of 112.5 mL and the yellow solution was stirred under nitrogen overnight at 50° C. (bath). Karl Fischer titration showed 0.091% water.

1. customIn a separate 250-mL round-bottom flask equipped with a magnetic stir bar
2. temperaturewhile maintaining the reaction temperature at <99° C
3. additionOn completion of the addition
4. stirringthe mixture was stirred at 70 to 75° C. for 15 minutes before the phases
5. customwere separated at room temperature
6. extractionThe upper aqueous phase was extracted with toluene (2×25 mL) at 70 to 75° C
7. washThen, the combined organic phases were washed with water (2×25 mL) at 70 to 75° C.
8. concentrationconcentrated by distillation under reduced pressure at 60° C. (bath)
9. additionThe residue was diluted with toluene to a total volume of 112.5 mL
10. stirringthe yellow solution was stirred under nitrogen overnight at 50° C. (bath)

ORD record

ord-8ffca06d417b4c328a13ca1ccfef749e

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2