Epichlorohydrin → 1-[(Oxiran-2-yl)methyl]piperidine

Piperidine (3 ml) was dissolved in t-butyl alcohol (1.2 ml), and the solution was added dropwise with (±)-epichlorohydrin (2.45 ml) on an ice bath. The mixture was slowly warmed to room temperature as it was, and stirred for 18 hours. Then, the mixture was added dropwise with a solution of potassium t-butoxide (3.39 g) in tetrahydrofuran (18 ml) under ice cooling so that the internal temperature should not exceed 15° C. After the addition, the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was added to distilled water, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to obtain the title compound (1.55 g).

1. customexceed 15° C
2. additionAfter the addition
3. stirringthe reaction mixture was stirred at room temperature for 2 hours
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additionthe resulting residue was added
6. distillationto distilled water
7. extractionthe mixture was extracted with chloroform
8. washThe organic layer was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure
12. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

ORD record

ord-4fb34474566e496d9be72f20b7ea5835

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097708B2