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

HRID 339448Notes

Reaction equation

HRID 339448 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.O.[NH2:10][NH2:11]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[N:10][NH2:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 740491-Methyl-4-piperidone

Product 1

HCID 45087302HCID 45087302, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-533d9d7b22b448009306e76878b4f834
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

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