反应详情

温度

75 °C

A solution of 1-(4-pyridyl)piperidine-4-methanol (5.87 g, 30.6 mmol), phthalimide (4.59 g, 31.2 mmol), and triphenylphosphine (8.10 g, 30.9 mmol) in 125 mL of THF at −5° C. was treated with a solution of diethyl azodicarboxylate (5.38 g, 30.9 mmol) in THF (40 mL). After 16 h, the mixture was poured into EtOAc and 1 N HCl. The aqueous layer was washed with EtOAc (2×), pH adjusted to 12 by addition of 5 N NaOH, and washed with EtOAc (3×). The combined organic extracts were dried (K2CO3) and concentrated, yielding 8.45 g (86%). The crude material (5.47 g, 17.0 mmol) was then treated with hydrazine hydrate (3.5 mL, 60.0 mmol) in EtOH (50 ML). The mixture was heated at 75° C. for 5 h, cooled, diluted with CH2Cl2 (100 mL), and cooled to 0° C. The solid was removed by filtration; and the filtrate was concentrated, yielding 3.32 g of the title compound which was used without further purification.

1. washThe aqueous layer was washed with EtOAc (2×)
2. additionpH adjusted to 12 by addition of 5 N NaOH
3. washwashed with EtOAc (3×)
4. dry with materialThe combined organic extracts were dried (K2CO3)
5. concentrationconcentrated
6. customyielding 8.45 g (86%)
7. temperaturecooled
8. temperaturecooled to 0° C
9. customThe solid was removed by filtration
10. concentrationand the filtrate was concentrated