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

Temperature

120 °C

In a 500-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to a caustic scrubber, 1-aminopropan-2-ol (60.2 g, 802 mmol) was heated to 120° C. The solution of 1-chloro-4-(2-chloroethyl)benzene in toluene prepared in Step A was added dropwise over 70 min at 114° C. to 120° C. and upon completion of the addition, the mixture was stirred at reflux for a further 2 h and then allowed to cool to 72° C. Aqueous NaOH (50%, 12.83 g, 160 mmol) and water (25 mL) were added and the mixture was stirred at 70 to 73° C. for approximately 5 minutes. The phases were allowed to separate, the aqueous phase was removed, and the organic phase washed at 80° C. (bath) for approximately 5 min with water (4×25 mL). The combined aqueous phases were extracted with toluene (37 mL) at 80° C. (bath). The combined organic phases were concentrated under reduced pressure at 60° C. (bath) and then at room temperature overnight to leave the title compound as a white solid.

1. customIn a 500-mL round-bottom flask equipped with magnetic stirring
2. temperatureat reflux for a further 2 h
3. temperatureto cool to 72° C
4. stirringthe mixture was stirred at 70 to 73° C. for approximately 5 minutes
5. customto separate
6. customthe aqueous phase was removed
7. washthe organic phase washed at 80° C. (bath) for approximately 5 min with water (4×25 mL)
8. extractionThe combined aqueous phases were extracted with toluene (37 mL) at 80° C. (bath)
9. concentrationThe combined organic phases were concentrated under reduced pressure at 60° C. (bath)

ORD record

ord-b3942c0fc8244c91a7ff14a5de1632f3

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2