Triethylamine → HCID 23079676, compound

(4-Benzylmorpholin-3-yl)methanol (3.00 g, 22.9 mmol) described in Journal of Chemical Society, Perkin Transactions 1, p. 2577 (1985) was dissolved in tetrahydrofuran (5 mL), and the solution was mixed with triethylamine (6.30 mL, 49.2 mmol) and methanesulfonic anhydride (3.20 g, 18.5 mmol), followed by stirring at room temperature for two hours. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was mixed with chloroform (50 mL) and a saturated aqueous sodium bicarbonate solution (50 mL), followed by separation. The organic layer was washed with brine (100 mL), was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting pale yellow oil was dissolved in dioxane (50 mL), and the solution was mixed with tert-butyl 1-piperazinecarboxylate (3.44 g, 18.5 mmol) and sodium carbonate (19.6 g, 185 mmol), followed by stirring at 80° C. for eighteen hours. After standing to cool, the reaction mixture was mixed with chloroform (50 mL) and water (50 mL), followed by separation. The organic layer was washed with brine (100 mL), was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting brown oil was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and thereby yielded tert-butyl 4-(4-benzylmorpholin-3-ylmethyl)piperazinecarboxylate (2.79 g, 60%).

1. customthe completion of the reaction by thin layer chromatography
2. customa saturated aqueous sodium bicarbonate solution (50 mL), followed by separation
3. washThe organic layer was washed with brine (100 mL)
4. dry with materialwas dried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. dissolutionThe resulting pale yellow oil was dissolved in dioxane (50 mL)
7. stirringby stirring at 80° C. for eighteen hours
8. temperatureto cool
9. customfollowed by separation
10. washThe organic layer was washed with brine (100 mL)
11. dry with materialwas dried over anhydrous magnesium sulfate
12. distillationthe solvent was distilled off under reduced pressure
13. customThe resulting brown oil was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-9139c6ade1404ce496fe17a47928f7b1

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524852B2