tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate → tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Temperature

100 °C

The compound (0.77 g) obtained in the above (4) is dissolved in DMF (5 ml), and thereto is added potassium phthalimide (0.537 g), and the mixture is stirred at 100° C. for 1.5 hour. The reaction mixture is diluted with water, and extracted three times with ethyl acetate. The extract is washed successively with 1N hydrochloric acid (twice), a saturated brine (once), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and dried over anhydrous magnesium sulfate. The desiccant is removed by the filtration, and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethanol (20 ml) and thereto is added hydrazine monohydrate (2.3 g) and the mixture is stirred at room temperature for 48 hours. The mixture is diluted with ether, and the insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (0.63 g) as an oily product.

1. extractionextracted three times with ethyl acetate
2. washThe extract is washed successively with 1N hydrochloric acid (twice), a saturated brine (once), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe desiccant is removed by the filtration
5. concentrationthe filtrate is concentrated under reduced pressure
6. dissolutionThe residue is dissolved in ethanol (20 ml)
7. additionis added hydrazine monohydrate (2.3 g)
8. stirringthe mixture is stirred at room temperature for 48 hours
9. additionThe mixture is diluted with ether
10. customthe insoluble materials are removed by filtration
11. concentrationthe filtrate is concentrated under reduced pressure

ORD record

ord-3f7f24f51812423d90272785a4ac5c24

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05707994