Morpholine → 4-((4-(Bromomethyl)phenyl)sulfonyl)morpholine

To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+.

1. extractionextracted with ethyl acetate (2×30 mL)
2. washThe combined organic layers were washed with water, brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customSolvents were removed
6. customto yield an orange oil, which
7. customwas purified on a 40 g silica gel column

ORD-Eintrag

ord-13b4849bbc1a40dda980430c6255df12

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08658129B2