Morpholine → HCID 22285325, compound

To 5-bromo-2-fluorobenzaldehyde (2.50 g, 12 mmol) and morpholine (1.61 mL, 1.61 g, 18 mmol) in 1,2-dichloroethane (100 mL) was added sodium triacetoxyborohydride (5.21 g, 2.5 mmol) portionwise with stirring at room temperature over 5 min. The mixture was stirred under nitrogen for 1 h, then 2 N sodium hydroxide solution (100 mL) was added, and the mixture was stirred for a further 5 min. The biphasic mixture was separated, and the aqueous layer was washed with dichloromethane (2×75 mL). The combined organic layers were washed with saturated sodium chloride solution (1×50 mL) and were concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 75% diethyl ether in isohexane (+1% triethylamine), to yield 4-(5-bromo-2-fluorobenzyl)morpholine (3.18 g, 94%).

1. stirringThe mixture was stirred under nitrogen for 1 h
2. stirringthe mixture was stirred for a further 5 min
3. customThe biphasic mixture was separated
4. washthe aqueous layer was washed with dichloromethane (2×75 mL)
5. washThe combined organic layers were washed with saturated sodium chloride solution (1×50 mL)
6. concentrationwere concentrated in vacuo
7. customThe crude product was purified by flash chromatography on silica gel
8. washeluting with 75% diethyl ether in isohexane (+1% triethylamine)

ORD record

ord-db1dcf685ff54f64b8305787f0979aec

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960598B2