Benzylamine → 2-Benzylamino-1-(4-octyloxy-phenyl)ethanol

To a cooled (0° C.) suspension of 2-Bromo-1-(4-octyloxy-phenyl)-ethanone (36.1 g; 110.3 mmol) in EtOH (500 mL) and CHCl3 (100 mL) was added benzylamine (48.2 mL; 441.2 mmol). After 30 minutes the ice-bath was removed and the mixture stirred for another 2 hours at RT. Subsequently the reaction mixture was cooled again to 0° C. and NaBH4 (6.26 g; 165.5 mmol) was added in small portions. The resulting mixture was stirred at 0° C. for 1 hour and thereafter another 4 hours at RT. The reaction mixture was quenched with 1M aqueous HCl (750 mL) at 0° C. and stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 2 N aqueous NaOH. The organic layer was dried (Na2SO4), filtered, concentrated in vacuo, and purified by column chromatography (SiO2, EtOAc) to give 2-benzylamino-1-(4-octyloxy-phenyl)-ethanol (22.58 g)

1. temperatureTo a cooled
2. customAfter 30 minutes the ice-bath was removed
3. temperatureSubsequently the reaction mixture was cooled again to 0° C.
4. stirringThe resulting mixture was stirred at 0° C. for 1 hour
5. customanother 4 hours
6. customat RT
7. customThe reaction mixture was quenched with 1M aqueous HCl (750 mL) at 0° C.
8. stirringstirred at RT for 1 hour
9. concentrationThe reaction mixture was concentrated in vacuo
10. customthe residue was partitioned between EtOAc and 2 N aqueous NaOH
11. dry with materialThe organic layer was dried (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. custompurified by column chromatography (SiO2, EtOAc)

ORD record

ord-ddf31205701343fabcf7104047482cc0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273017B2