Morpholine → HCID 66878651, compound

(Step 1) To a solution of morpholine (0.36 ml) and triethylamine (0.58 ml) in methanol (15 ml) was added dropwise a suspension of 2-[(acetylamino)methyl]-4-fluorobenzenesulfonyl chloride (1.00 g) in tetrahydrofuran (5 ml) under ice-cooling, and the mixture was allowed to warm to room temperature, and stirred for 1 hr. The reaction mixture was quenched with saturated brine, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate). The obtained oil was dissolved in ethanol (20 ml), hydrochloric acid (10 ml) was added, and the mixture was stirred with heating under reflux for 9 hr. The solvent was evaporated under reduced pressure, and the residue was collected by filtration, and washed with ethyl acetate to give 1-[5-fluoro-2-(morpholin-4-ylsulfonyl)phenyl]methanamine hydrochloride (0.58 g) as a white solid.

1. temperaturecooling
2. customThe reaction mixture was quenched with saturated brine
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel chromatography (ethyl acetate)
8. dissolutionThe obtained oil was dissolved in ethanol (20 ml)
9. additionhydrochloric acid (10 ml) was added
10. stirringthe mixture was stirred
11. temperaturewith heating
12. temperatureunder reflux for 9 hr
13. customThe solvent was evaporated under reduced pressure
14. filtrationthe residue was collected by filtration
15. washwashed with ethyl acetate

ORD record

ord-01150b87a10547198ac26b49d0ad4465

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985863B2