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

HRID 1184299Notes

Reaction equation

HRID 1184299 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-628d05016e82444f95d88bec852bda6b
Source dataset
uspto-grants-2014_03
Patent number
US08669072B2

Reaction notes

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