Sodium Methoxide → 2-Dimethylamino-2-methoxy-1-methylpyrrolidine

HRID 1278072Notes

Reaction equation

HRID 1278072 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH2:7][CH2:6][CH2:5][N+:4]=1[CH3:8].[CH3:10][O:11]S([O-])(=O)=O.C[O-].[Na+]>C(OCC)C>[CH3:1][N:2]([CH3:9])[C:3]1([O:11][CH3:10])[CH2:7][CH2:6][CH2:5][N:4]1[CH3:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Product 1

HCID 234525542-Dimethylamino-2-methoxy-1-methylpyrrolidineYield 27.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add (dropwise, at room temperature, with stirring) 50.0 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate to 12.65 g of sodium methylate, suspended in 120 ml of absolute diethyl ether and boil the resulting reaction mixture under reflux for 1 hour. After cooling the refluxed material, filter the precipitated salt therefrom. Draw off the ether from the filtrate and distil under a vacuum what remains of the filtrate to obtain 9.0 g of the title compound as a liquid (with a very marked tendency to decomposition) of b.p. 45° to 47° at 11 mm of Hg.

Workup

  1. additionAdd (dropwise, at room temperature
  2. customthe resulting reaction mixture
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter cooling the refluxed material
  5. filtrationfilter the precipitated salt
  6. customDraw off the ether from the filtrate and distil under a vacuum what

Sources & evidence

ORD record
ord-42e999d693bd456cad2694384d52836d
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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