Dimethylamine → 2-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

HRID 2049649Notes

Reaction equation

HRID 2049649 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].CO[C:9]1[CH2:13][CH2:12][CH2:11][N+:10]=1[CH3:14].[CH3:15][NH:16][CH3:17]>C1C=CC=CC=1>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[CH3:15][N:16]([CH3:17])[C:9]1[CH2:13][CH2:12][CH2:11][N+:10]=1[CH3:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 110533222-Methoxy-1-methyl-1-pyrrolinium methyl sulfate

Product 1

HCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

22.5 g of 2-methoxy-1-methyl-1-pyrrolinium methyl sulfate are added dropwise (with stirring) to a solution of 6.76 g of dimethylamine in 45 ml of benzene. The resulting admixture is subsequently boiled under reflux for 1 hour. The obtained heavy phase is separated off, extracted twice by shaking with diethyl ether and freed from solvent residues in a vacuum. 19.4 g (81.4% of theory) of the title compound (as a red-brown oil) are thus obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe obtained heavy phase is separated off
  3. extractionextracted twice

Sources & evidence

ORD record
ord-fc8a774637594caaa6353b059bbb08c2
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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