Hydrazine hydrate (1:1) → HCID 45087302, compound

1-Methyl-piperidin-4-one (22.6 g, 0.2 mol) and methanol (200 mL) were charged to a 500 mL three-necked flask fitted with an addition funnel. The vessel was cooled in an ice bath and kept under a nitrogen atmosphere while a solution of hydrazine monohydrate (5 g, 0.1 mol) in 50 mL of methanol was added drop-wise over a period of one hour. A white precipitate formed after about half of the hydrazine was added. Stirring was continued overnight, and subsequent TLC indicated one product. The methanol was removed in vacuo, and the residue was slurried in hexane and filtered to provide N,N′-bis-(1-methyl-piperidin-4-ylidene)-hydrazine. 1H NMR (300 MHz, CDCl3)δ(ppm): 2.6 (m, 8H), 2.5 (m, 8H), 2.33 (s, 6H).

1. customfitted with an addition funnel
2. temperatureThe vessel was cooled in an ice bath
3. additionwas added drop-wise over a period of one hour

ORD record

ord-d2abc78839e345788330df381e963520

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304162B2