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

Temperature

90 °C

A 1-L jacketed reactor was equipped with a retreat curve stir blade, overhead stirring, a thermocouple, a condenser, and a nitrogen bubbler. 1-Aminopropan-2-ol (110 mL, 1429 mmol) was added and heated to 85 and 90° C. 1-Chloro-4-(2-chloroethyl)benzene (50.032 g, 286 mmol) was added over 1 h at <97° C. and upon completion of the addition stirring was continued at 90 to 95° C. for 2.5 h. The internal temperature was reduced to 75° C. and chlorobenzene (100 mL) and water (50 mL) were added. The mixture was stirred for 15 min at 70 to 75° C. before the phases were separated. The upper aqueous phase was extracted with chlorobenzene at 70 to 75° C. (2×50 mL). The combined organic phases were washed with water at 70-75° C. (2×50 mL) and then held over the weekend at room temperature. The solution was then concentrated at 60 to 65° C. (bath) at 40 to 45 mbar to remove 143 g of distillate.

1. customA 1-L jacketed reactor was equipped with a retreat curve
2. stirringoverhead stirring
3. stirringstirring
4. customwas reduced to 75° C.
5. stirringThe mixture was stirred for 15 min at 70 to 75° C. before the phases
6. customwere separated
7. extractionThe upper aqueous phase was extracted with chlorobenzene at 70 to 75° C. (2×50 mL)
8. washThe combined organic phases were washed with water at 70-75° C. (2×50 mL)
9. customheld over the weekend at room temperature
10. concentrationThe solution was then concentrated at 60 to 65° C. (bath) at 40 to 45 mbar
11. customto remove 143 g of distillate

ORD record

ord-a3e85dca1c4b473d969ff36df153a28e

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2