Carbon Dioxide → 2-Aminomethyl-1-ethylpyrrolidine

HRID 258797Notes

Reaction equation

HRID 258797 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O.[CH2:10]([N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[CH:17][N+:18]([O-])=O)[CH3:11]>[Cu].[Pd].CO>[NH2:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:12]1[CH2:10][CH3:11]

Participants

7

Reactant 3

HCID 280Carbon Dioxide2×HCID 10340Sodium Carbonate2×HCID 11774426171-04-0

Product 1

HCID 1172952-Aminomethyl-1-ethylpyrrolidineYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

A 200 ml. glass beaker having inserted therein a porous unglazed cylinder (40 mm. diameter × 140 mm. length) was used as the electrolytic apparatus and a copper plate (40 × 180 mm2) as the cathode and a palladium plate (30 × 40 mm2) as the anode were used. In the anode chamber (the porous unglazed cylinder) was added 50 ml. of a saturated aqueous sodium carbonate solution and in the cathode chamber (the glass beaker) were added 70 ml. of a 2 N aqueous sodium carbonate solution and 30 ml. of methanol. Then, after carrying out pre-electrolysis for several minutes while passing carbon dioxide through the catholyte solution, 1.56 g. of the powder of 1-ethyl-2-nitromethylenepyrrolidine was added to the cathode chamber and current of 1 ampere was electrified for 2.5 hours with stirring at 20°-23° C. while passing carbon dioxide through the catholyte solution to carry out the electrolysis. Then, by treating the product as in Example 1, 1.22 g. of oily 2-aminomethyl-1-ethylpyrrolidine was obtained with a yield of 95%.

Workup

  1. additionIn the anode chamber (the porous unglazed cylinder) was added 50 ml
  2. waitThen, after carrying out pre-electrolysis for several minutes
  3. additionThen, by treating the product as in Example 1, 1.22 g

Sources & evidence

ORD record
ord-7791c21d085f432cbe017fff59e1c30d
Source dataset
uspto-grants-1977_07
Patent number
US04035252

Reaction notes

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