1,2-Diethylhydrazine dihydrochloride → HCID 10442180, compound

HRID 2198568Notes

Reaction equation

HRID 2198568 reaction equation
Cl.Cl.C(NNCC)C.O1CC[N:12]([CH2:15][CH:16]([N+:24]([O-:26])=[O:25])[CH2:17][N:18]2CCO[CH2:20][CH2:19]2)[CH2:11][CH2:10]1>CO.C1(C)C=CC=CC=1>[N+:24]([CH:16]1[CH2:15][N:12]([CH2:11][CH3:10])[N:18]([CH2:19][CH3:20])[CH2:17]1)([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 243721,2-Diethylhydrazine dihydrochlorideHCID 6881101,3-DIMORPHOLINO-2-NITROPROPANE

Product 1

HCID 10442180HCID 10442180, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A stirred solution of 4.03 g (0.025 moles) of 1,2-diethylhydrazine dihydrochloride and 6.72 g. (0.026 moles) of 1,3-dimorpholino-2-nitropropane in a mixture of 28 ml of methanol and 16 ml of toluene was heated at reflux for 3 hours. The solvents were evaporated under reduced pressure and the residue was resuspended in 100 ml of toluene. The solid morpholine hydrochloride was removed by filtration, leaving a solution of 4-nitro-1,2-diethyl-pyrazolidine in solution. To the toluene solution was added 60 ml anhydrous ethanol and 2 g. of Raney Nickel which had been washed three times with anhydrous ethanol. The mixture was hydrogenated at about 30 psi. hydrogen pressure. The mixture was filtered carefully under nitrogen to prevent ignition. Evaporation of solvents and distillation at reduced pressure gave colorless liquid product weighing 1.95 g. (54% yield calculated on diethylhydrazine), b.p. 113°-115° C./40 mm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe solvents were evaporated under reduced pressure
  4. customThe solid morpholine hydrochloride was removed by filtration

Sources & evidence

ORD record
ord-a08ecb7e867a41efb1724c3583f8e133
Source dataset
uspto-grants-1982_11
Patent number
US04358599

Reaction notes

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