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

Temperature

90 °C

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.

1. customInto a 1-L jacketed reactor equipped with a retreat curve
2. stirringoverhead stirring
3. stirringStirring
4. stirringthe mixture was stirred at 70 to 75° C. for 15 min
5. customto separate
6. extractionthe aqueous phase was extracted with chlorobenzene (2×50 mL) at 70 to 75° C
7. washThe combined organic phases were then washed with water (2×50 mL) at 70 to 75° C.
8. concentrationconcentrated by distillation under reduced pressure
9. dissolutionThe residue was dissolved in chlorobenzene to a total weight of 503 g
10. waitto stand at room temperature overnight
11. customA solid precipitate formed which
12. dissolutionwas redissolved
13. temperatureheating the mixture at 30 to 35° C.

ORD record

ord-1311db2abbee4b6093f217a94b6e6f27

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2