Hydrazine → 2-(4-Hydroxypiperidin-1-yl)acetohydrazide

Temperature

85 °C

To a solution of 4-hydroxypiperidine (1.1 g, 0.011 mol) and potassium carbonate (1.52 g, 0.011 mol) in acetonitrile (˜20 mL) was added methylbromoacetate (0.93 mL, 0.01 mol) and the mixture was stirred in a nitrogen atmosphere overnight. The solvent was removed and the material was taken up in methanol. Gaseous hydrochloric acid was bubbled into solution. The methanol was removed and the material was taken up in tetrahydrofuran and sonicated. A solid was collected using a fritted funnel. The solid was taken up in ethyl acetate. Sodium carbonate was added to the solution and allowed to stir for one hour. The sodium carbonate was removed by filtration and the organic layer was concentrated. A solution of the crude material was made using anhydrous ethanol (˜1 mL) and hydrazine (0.167 mL, 5.34 mmol). This was placed in a sealed tube and was heated to 85° C. for 3 hours. The solvent was removed to yield the title compound (0.875 g, 50% yield). 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 4.6 (s, 1H), 4.2 (s, 2H), 2.8 (s, 2H), 2.6 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H), 1.4 (m, 2H).

1. customThe solvent was removed
2. customGaseous hydrochloric acid was bubbled into solution
3. customThe methanol was removed
4. customsonicated
5. customA solid was collected
6. additionSodium carbonate was added to the solution
7. stirringto stir for one hour
8. customThe sodium carbonate was removed by filtration
9. concentrationthe organic layer was concentrated
10. customThis was placed in a sealed tube
11. customThe solvent was removed

ORD record

ord-6b188a0988e34ecb81c74074f40d2eba

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220771B2