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

HRID 1278029Notes

Reaction equation

HRID 1278029 reaction equation
CO[C:3]1[CH2:7][CH2:6][CH2:5][N+:4]=1[CH3:8].[CH3:9][O:10][S:11]([O-:14])(=[O:13])=[O:12].[CH3:15][NH:16][CH3:17]>C1C=CC=CC=1>[CH3:15][N:16]([CH3:17])[C:3]1[CH2:7][CH2:6][CH2:5][N+:4]=1[CH3:8].[CH3:9][O:10][S:11]([O-:14])(=[O:13])=[O:12]

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

Add dropwise, with stirring, 22.5 g of 2-methoxy-1-methyl-1-pyrrolinium-methylsulfate to a solution of 6.76 g of dimethylamine in 45 ml of benzene and then boil the obtained admixture under reflux for 1 hour. Separate off the resulting heavy phase; extract it twice by shaking it out with diethyl ether and then free the extract from solvent residue in a vacuum to obtain 19.4 g (81.4% of theory) of title compound as reddish brown oil.

Workup

  1. additionAdd dropwise
  2. temperatureunder reflux for 1 hour
  3. customSeparate off the resulting heavy phase
  4. extractionextract it twice
  5. stirringby shaking it out with diethyl ether
  6. extractionextract from solvent residue in a vacuum

Sources & evidence

ORD record
ord-be63aefe6d4f4b66a8bf8cc8ee15d958
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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