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

Temperature

90 °C

In a 500-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 (96 g, 1277 mmol). This was heated in oil bath at 90° C. and the solution of chloro-4-(2-chloroethyl)benzene from Step A was slowly added over 1.25 h at a maximum temperature of 95° C. The reaction was stirred at 90 to 95° C. for 2 h and then toluene (80 mL) and water (40 mL) were added. The mixture was stirred for 15 min at 70 to 80° C. and then the phases were allowed to separate at room temperature. The aqueous phase was extracted with toluene (2×40 mL). The combined toluene phases were washed with water (2×40 mL) at 70 to 80° C. and then concentrated under reduced pressure at 60° C. Toluene was added to the residue to give a total volume of 170 mL and the solution was stirred overnight at 55° C. (bath). This solution was found to contain 0.052% water by Karl Fischer titration.

1. customIn a 500-mL round-bottom flask equipped with a magnetic stir bar
2. stirringThe mixture was stirred for 15 min at 70 to 80° C.
3. customto separate at room temperature
4. extractionThe aqueous phase was extracted with toluene (2×40 mL)
5. washThe combined toluene phases were washed with water (2×40 mL) at 70 to 80° C.
6. concentrationconcentrated under reduced pressure at 60° C
7. additionToluene was added to the residue
8. customto give a total volume of 170 mL
9. stirringthe solution was stirred overnight at 55° C. (bath)

ORD record

ord-7ea2a24d57bc483e983a147b32634e98

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2