Benzyl Bromide → 4-Benzyl-2,6-dimethylmorpholine

To a tetrahydrofuran solution (500 mL) of 2,6-dimethylmorpholine (Aldrich Co.) (mixture of cis/trans isomers) (25.02 g, 217.24 mmol), triethylamine (51.48 mL, 369.31 mmol) was added at room temperature, and the mixture was stirred for 15 minutes. Then, benzyl bromide (43.93 mL, 369.31 mmol) was added dropwise over 30 minutes, and the mixture was stirred for 4 days. A saturated aqueous solution of sodium hydrogen carbonate (200 mL) was added to the reaction liquor, and the mixture was stirred for 30 minutes, and then extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 65i, n-hexane to ethyl acetate/n-hexane 1:1), to obtain the title compound (10.7 g, 24%) as an oily matter.

1. stirringthe mixture was stirred for 4 days
2. stirringthe mixture was stirred for 30 minutes
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationthe solvent was concentrated under reduced pressure
7. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 65i, n-hexane to ethyl acetate/n-hexane 1:1)

ORD record

ord-b8f5a7f863b6490a85c8dd4af515e99f

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129366B2