Iodoethane → 1-Ethyl-4-nitroxypiperidine fumarate

HRID 1086490Notes

Reaction equation

HRID 1086490 reaction equation
[O:1]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[N+:2]([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH3:18].[C:20]([O-:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([O-:25])=[O:24]>CC(C)=O>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[CH2:17]([N:8]1[CH2:9][CH2:10][CH:5]([O:1][N+:2]([O-:4])=[O:3])[CH2:6][CH2:7]1)[CH3:18]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5460307FumarateHCID 15068866HCID 15068866, compound

Product 1

HCID 867448961-Ethyl-4-nitroxypiperidine fumarate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.9 g. 4-Nitroxypiperidine are dissolved in 50 ml. acetone, mixed with 13.8 g. potassium carbonate and 6.1 ml. ethyl iodide and stirred for 18 hours at ambient temperature. After filtering with suction, the filtrate is evaporated, the residue is dissolved in ethyl acetate and extracted twice with aqueous sodium chloride solution. The orgainc phase is dried with anhydrous sodium sulphate. The crude product (8.2 g.) remaining after suction filtration and evaporation is converted into the fumarate by dissolving in ethanol and adding 2.7 g. fumaric acid. After filtering off with suction, there are obtained 2.6 g. of the fumarate of the title compound, i.e. 23% of theory; m.p. 131°-134° C.

Workup

  1. filtrationAfter filtering with suction
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. extractionextracted twice with aqueous sodium chloride solution
  5. dry with materialThe orgainc phase is dried with anhydrous sodium sulphate
  6. filtrationafter suction filtration and evaporation
  7. dissolutionby dissolving in ethanol
  8. additionadding 2.7 g
  9. filtrationAfter filtering off with suction, there
  10. customare obtained 2.6 g

Sources & evidence

ORD record
ord-b2dab2d39ef8479eacbbd4585a6d4e18
Source dataset
uspto-grants-1991_07
Patent number
US05030641

Reaction notes

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